JP5325297B2 - 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 - Google Patents
農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 Download PDFInfo
- Publication number
- JP5325297B2 JP5325297B2 JP2011522855A JP2011522855A JP5325297B2 JP 5325297 B2 JP5325297 B2 JP 5325297B2 JP 2011522855 A JP2011522855 A JP 2011522855A JP 2011522855 A JP2011522855 A JP 2011522855A JP 5325297 B2 JP5325297 B2 JP 5325297B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- linear
- branched
- ring
- 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.)
- Expired - Fee Related
Links
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 41
- KRQZDCVCBATZEZ-UHFFFAOYSA-N 4-but-3-ynylpyrimidin-2-amine Chemical class C(CC#C)C1=NC(=NC=C1)N KRQZDCVCBATZEZ-UHFFFAOYSA-N 0.000 title claims description 14
- -1 for example Chemical group 0.000 claims abstract description 230
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 223
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 125
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
- 125000005843 halogen group Chemical group 0.000 claims abstract description 49
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 29
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 13
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- XSBPYGDBXQXSCU-UHFFFAOYSA-N but-3-yn-1-amine Chemical class NCCC#C XSBPYGDBXQXSCU-UHFFFAOYSA-N 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 150000003949 imides Chemical class 0.000 claims description 7
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 150000004292 cyclic ethers Chemical class 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- TWTODSLDHCDLDR-UHFFFAOYSA-N 4-chlorothieno[3,2-d]pyrimidine Chemical class ClC1=NC=NC2=C1SC=C2 TWTODSLDHCDLDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000005311 halosulfanyl group Chemical group 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 1
- MNFANLSWHUFVTL-UHFFFAOYSA-N n-but-3-ynylpyrimidin-4-amine Chemical class C#CCCNC1=CC=NC=N1 MNFANLSWHUFVTL-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
- 239000000243 solution Substances 0.000 description 94
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
- 125000003545 alkoxy group Chemical group 0.000 description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 201000010099 disease Diseases 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- 238000001914 filtration Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 21
- 241000234282 Allium Species 0.000 description 20
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000001816 cooling Methods 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 240000008067 Cucumis sativus Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 206010027146 Melanoderma Diseases 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 241000123650 Botrytis cinerea Species 0.000 description 14
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 14
- 241000221785 Erysiphales Species 0.000 description 14
- 235000014443 Pyrus communis Nutrition 0.000 description 14
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- 241001529387 Colletotrichum gloeosporioides Species 0.000 description 13
- 206010035148 Plague Diseases 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 241000237502 Ostreidae Species 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 235000020636 oyster Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000004563 wettable powder Substances 0.000 description 12
- 235000006040 Prunus persica var persica Nutrition 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 235000016623 Fragaria vesca Nutrition 0.000 description 10
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 229930192474 thiophene Natural products 0.000 description 10
- 240000006108 Allium ampeloprasum Species 0.000 description 9
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 9
- 241000207199 Citrus Species 0.000 description 9
- 235000020971 citrus fruits Nutrition 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 238000001308 synthesis method Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 244000144730 Amygdalus persica Species 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- 240000009088 Fragaria x ananassa Species 0.000 description 8
- 206010039509 Scab Diseases 0.000 description 8
- 241000576755 Sclerotia Species 0.000 description 8
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 241000238876 Acari Species 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 241000223221 Fusarium oxysporum Species 0.000 description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 241000233679 Peronosporaceae Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 240000003768 Solanum lycopersicum Species 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YIMNQWSIQLKYOZ-UHFFFAOYSA-N 2-but-3-ynylisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N(CCC#C)C(=O)C2=C1 YIMNQWSIQLKYOZ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- 235000002597 Solanum melongena Nutrition 0.000 description 6
- 244000061458 Solanum melongena Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 150000001345 alkine derivatives Chemical class 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension 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
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- 241000239290 Araneae Species 0.000 description 5
- 235000005340 Asparagus officinalis Nutrition 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 241001070941 Castanea Species 0.000 description 5
- 235000014036 Castanea Nutrition 0.000 description 5
- 241000219109 Citrullus Species 0.000 description 5
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 244000193174 agave Species 0.000 description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 description 4
- NZCRUBBNZGVREM-UHFFFAOYSA-N 4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CS2 NZCRUBBNZGVREM-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 235000002566 Capsicum Nutrition 0.000 description 4
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 4
- 241000219112 Cucumis Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- 244000000626 Daucus carota Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 239000005567 Imazosulfuron Substances 0.000 description 4
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 description 4
- 244000017020 Ipomoea batatas Species 0.000 description 4
- 235000002678 Ipomoea batatas Nutrition 0.000 description 4
- DGYHPLMPMRKMPD-UHFFFAOYSA-N L-propargyl glycine Natural products OC(=O)C(N)CC#C DGYHPLMPMRKMPD-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000006002 Pepper Substances 0.000 description 4
- 235000006089 Phaseolus angularis Nutrition 0.000 description 4
- 235000016761 Piper aduncum Nutrition 0.000 description 4
- 240000003889 Piper guineense Species 0.000 description 4
- 235000017804 Piper guineense Nutrition 0.000 description 4
- 235000008184 Piper nigrum Nutrition 0.000 description 4
- 241001246058 Puccinia allii Species 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 240000007098 Vigna angularis Species 0.000 description 4
- 235000010711 Vigna angularis Nutrition 0.000 description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 208000024386 fungal infectious disease Diseases 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000004071 soot Substances 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 3
- MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical compound BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 3
- PXRSHSUMZYVCDS-UHFFFAOYSA-N 2-(2-phenylethynyl)but-3-en-1-ol Chemical compound OCC(C=C)C#CC1=CC=CC=C1 PXRSHSUMZYVCDS-UHFFFAOYSA-N 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- 235000000832 Ayote Nutrition 0.000 description 3
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 3
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 3
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 3
- 240000004160 Capsicum annuum Species 0.000 description 3
- 235000007862 Capsicum baccatum Nutrition 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 241000222199 Colletotrichum Species 0.000 description 3
- 240000004244 Cucurbita moschata Species 0.000 description 3
- 235000009854 Cucurbita moschata Nutrition 0.000 description 3
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 3
- 235000002767 Daucus carota Nutrition 0.000 description 3
- 239000005781 Fludioxonil Substances 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 3
- 241000256602 Isoptera Species 0.000 description 3
- 229920002752 Konjac Polymers 0.000 description 3
- 241000255908 Manduca sexta Species 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 241001518731 Monilinia fructicola Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241001149949 Phytophthora cactorum Species 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 240000005809 Prunus persica Species 0.000 description 3
- 241000825108 Schizothyrium pomi Species 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 3
- 239000005839 Tebuconazole Substances 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 3
- 239000001728 capsicum frutescens Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- DSJCIGZFDWKYON-UHFFFAOYSA-N ethyl 4-phenyl-2-[(quinazolin-4-ylamino)methyl]but-3-ynoate Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C(=O)OCC)C#CC1=CC=CC=C1 DSJCIGZFDWKYON-UHFFFAOYSA-N 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 235000015136 pumpkin Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- NAEZQVWAWSVOSD-UHFFFAOYSA-N -14-Methyl-1-octadecene Natural products CCCCC(C)CCCCCCCCCCCC=C NAEZQVWAWSVOSD-UHFFFAOYSA-N 0.000 description 2
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 2
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DSPIWDJUDCTUMZ-UHFFFAOYSA-N 2-[2-(2-phenylethynyl)but-3-enyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(C=C)C#CC1=CC=CC=C1 DSPIWDJUDCTUMZ-UHFFFAOYSA-N 0.000 description 2
- MEUVNBVMEKRZKS-UHFFFAOYSA-N 2-benzyl-4-bromo-1,3-thiazole Chemical compound BrC1=CSC(CC=2C=CC=CC=2)=N1 MEUVNBVMEKRZKS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- SBUYFICWQNHBCM-UHFFFAOYSA-N 4-Ethyl-o-xylene Chemical compound CCC1=CC=C(C)C(C)=C1 SBUYFICWQNHBCM-UHFFFAOYSA-N 0.000 description 2
- XGBWZNGTYRKKFE-UHFFFAOYSA-N 4-bromo-2-phenyl-1,3-thiazole Chemical compound BrC1=CSC(C=2C=CC=CC=2)=N1 XGBWZNGTYRKKFE-UHFFFAOYSA-N 0.000 description 2
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 2
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 2
- 241000223602 Alternaria alternata Species 0.000 description 2
- 241001149961 Alternaria brassicae Species 0.000 description 2
- 241001157812 Alternaria brassicicola Species 0.000 description 2
- 241000795653 Alternaria cucumerina Species 0.000 description 2
- 241000212254 Alternaria porri Species 0.000 description 2
- 244000247812 Amorphophallus rivieri Species 0.000 description 2
- 235000001206 Amorphophallus rivieri Nutrition 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- 241000722809 Armadillidium vulgare Species 0.000 description 2
- 241001302798 Bemisia argentifolii Species 0.000 description 2
- 241000254127 Bemisia tabaci Species 0.000 description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 2
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241000145903 Bombyx mori cypovirus 1 Species 0.000 description 2
- 241000113236 Botryotinia allii Species 0.000 description 2
- 241000994678 Botryotinia squamosa Species 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- 241000243771 Bursaphelenchus xylophilus Species 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000906476 Cercospora canescens Species 0.000 description 2
- 241000437818 Cercospora vignicola Species 0.000 description 2
- 241001367803 Chrysodeixis includens Species 0.000 description 2
- BNHJLPUXLQGQAL-UHFFFAOYSA-N ClC=1C2=C(N=CN1)SC=C2.CN(C=O)C Chemical compound ClC=1C2=C(N=CN1)SC=C2.CN(C=O)C BNHJLPUXLQGQAL-UHFFFAOYSA-N 0.000 description 2
- 241001306234 Colletotrichum circinans Species 0.000 description 2
- 241000222235 Colletotrichum orbiculare Species 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 241001266001 Cordyceps confragosa Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- 239000005507 Diflufenican Substances 0.000 description 2
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 description 2
- 235000008597 Diospyros kaki Nutrition 0.000 description 2
- 244000236655 Diospyros kaki Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000995027 Empoasca fabae Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 241000423043 Eretmocerus eremicus Species 0.000 description 2
- 241000510928 Erysiphe necator Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 244000307700 Fragaria vesca Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001442497 Globodera rostochiensis Species 0.000 description 2
- 241000461774 Gloeosporium Species 0.000 description 2
- 241001502121 Glossina brevipalpis Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000498254 Heterodera glycines Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241001508566 Hypera postica Species 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000001126 Keratosis Diseases 0.000 description 2
- 241001177117 Lasioderma serricorne Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- 241001595366 Leucotelium pruni-persicae Species 0.000 description 2
- 240000001463 Mertensia maritima Species 0.000 description 2
- 235000014272 Mertensia maritima var. asiatica Nutrition 0.000 description 2
- 235000003168 Mertensia maritima var. maritima Nutrition 0.000 description 2
- 239000005807 Metalaxyl Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000006751 Mitsunobu reaction Methods 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241000819999 Nymphes Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001147398 Ostrinia nubilalis Species 0.000 description 2
- 239000005588 Oxadiazon Substances 0.000 description 2
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 2
- 241000223785 Paramecium Species 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000005816 Penthiopyrad Substances 0.000 description 2
- 241001670201 Peronospora destructor Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241001557902 Phomopsis sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 241001618091 Phyllactinia pyri Species 0.000 description 2
- 241001115351 Physalospora Species 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- 241000233616 Phytophthora capsici Species 0.000 description 2
- 239000005818 Picoxystrobin Substances 0.000 description 2
- 241000317981 Podosphaera fuliginea Species 0.000 description 2
- 241000896192 Podosphaera tridactyla Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241001341772 Pseudocercospora circumscissa Species 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 241000718000 Pulex irritans Species 0.000 description 2
- 241001136903 Rhagoletis pomonella Species 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- 241001480223 Steinernema carpocapsae Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 241000261593 Tyrophagus neiswanderi Species 0.000 description 2
- 241001669640 Venturia carpophila Species 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000005005 aminopyrimidines Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical class OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 2
- 229940056881 imidacloprid Drugs 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 2
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000252 konjac Substances 0.000 description 2
- 235000010485 konjac Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229930002897 methoprene Natural products 0.000 description 2
- 229950003442 methoprene Drugs 0.000 description 2
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- HVQLJVDRIAXJNZ-UHFFFAOYSA-N n-(1-phenylbut-3-ynyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(CC#C)C1=CC=CC=C1 HVQLJVDRIAXJNZ-UHFFFAOYSA-N 0.000 description 2
- DEGZVKJEKPQNSJ-UHFFFAOYSA-N n-(4-trimethylsilylbut-3-ynyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C[Si](C)(C)C#CCCNC1=NC=NC2=C1C=CS2 DEGZVKJEKPQNSJ-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 2
- 239000011591 potassium Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000005494 pyridonyl group Chemical group 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 241000701451 unidentified granulovirus Species 0.000 description 2
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- DBTMGCOVALSLOR-DEVYUCJPSA-N (2s,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@H](O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-DEVYUCJPSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- CSWBSLXBXRFNST-MQQKCMAXSA-N (8e,10e)-dodeca-8,10-dien-1-ol Chemical compound C\C=C\C=C\CCCCCCCO CSWBSLXBXRFNST-MQQKCMAXSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 description 1
- GSAAJQNJNPBBSX-UHFFFAOYSA-N (E)-form-9-Tetradecen-1-ol Natural products CCCCC=CCCCCCCCCO GSAAJQNJNPBBSX-UHFFFAOYSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- FZRBKIRIBLNOAM-UHFFFAOYSA-N (E,E)-2-propynyl 3,7,11-trimethyl-2,4-dodecadienoate Chemical compound CC(C)CCCC(C)CC=CC(C)=CC(=O)OCC#C FZRBKIRIBLNOAM-UHFFFAOYSA-N 0.000 description 1
- 239000005674 (E,E)-8,10-Dodecadien-1-ol Substances 0.000 description 1
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- HVUBXNQWXJBVHB-UHFFFAOYSA-N (Z)-13-Eicosen-10-one Natural products CCCCCCCCCC(=O)CCC=CCCCCCC HVUBXNQWXJBVHB-UHFFFAOYSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- UEIKOIYORDKQGZ-YPKPFQOOSA-N (z)-tetradec-1-en-1-ol Chemical compound CCCCCCCCCCCC\C=C/O UEIKOIYORDKQGZ-YPKPFQOOSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 description 1
- IHGSAQHSAGRWNI-UHFFFAOYSA-N 1-(4-bromophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Br)C=C1 IHGSAQHSAGRWNI-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- ULCWZQJLFZEXCS-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-5-(2,2,2-trifluoroethoxy)oxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(OCC(F)(F)F)CCC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ULCWZQJLFZEXCS-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- NFTOEHBFQROATQ-UHFFFAOYSA-N 2,3-dihydrofuran-5-carboxylic acid Chemical compound OC(=O)C1=CCCO1 NFTOEHBFQROATQ-UHFFFAOYSA-N 0.000 description 1
- NIOPZPCMRQGZCE-WEVVVXLNSA-N 2,4-dinitro-6-(octan-2-yl)phenyl (E)-but-2-enoate Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)\C=C\C NIOPZPCMRQGZCE-WEVVVXLNSA-N 0.000 description 1
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- NMCSRQBTYKNNDX-UHFFFAOYSA-N 2-(2-phenylethynyl)but-3-en-1-amine Chemical compound NCC(C=C)C#CC1=CC=CC=C1 NMCSRQBTYKNNDX-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- ZFIUWSUCQHNWIH-UHFFFAOYSA-N 2-(4-phenylbut-3-ynyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC#CC1=CC=CC=C1 ZFIUWSUCQHNWIH-UHFFFAOYSA-N 0.000 description 1
- DKYVXDQRBAVADI-UHFFFAOYSA-N 2-(5-phenylpent-4-yn-2-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C)CC#CC1=CC=CC=C1 DKYVXDQRBAVADI-UHFFFAOYSA-N 0.000 description 1
- HUASISNJODWVJZ-UHFFFAOYSA-N 2-(6-methylhept-3-ynyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCC#CCC(C)C)C(=O)C2=C1 HUASISNJODWVJZ-UHFFFAOYSA-N 0.000 description 1
- MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 description 1
- FJMWHFREXWQUNJ-UHFFFAOYSA-N 2-[4-(1,3-thiazol-2-yl)but-3-ynyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC#CC1=NC=CS1 FJMWHFREXWQUNJ-UHFFFAOYSA-N 0.000 description 1
- JDQZVLMTDIAUIA-UHFFFAOYSA-N 2-[4-(2-benzyl-1,3-thiazol-4-yl)but-3-ynyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC#CC(N=1)=CSC=1CC1=CC=CC=C1 JDQZVLMTDIAUIA-UHFFFAOYSA-N 0.000 description 1
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
- JUJBKWHHZNYPET-UHFFFAOYSA-N 2-[4-(2-phenoxy-1,3-thiazol-4-yl)but-3-ynyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC#CC(N=1)=CSC=1OC1=CC=CC=C1 JUJBKWHHZNYPET-UHFFFAOYSA-N 0.000 description 1
- LNKQFMOAFYUWSW-UHFFFAOYSA-N 2-[4-(2-phenyl-1,3-thiazol-4-yl)but-3-ynyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC#CC(N=1)=CSC=1C1=CC=CC=C1 LNKQFMOAFYUWSW-UHFFFAOYSA-N 0.000 description 1
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ITWJDWMHWRPGRX-UHFFFAOYSA-N 2-pent-4-yn-2-ylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(CC#C)C)C(=O)C2=C1 ITWJDWMHWRPGRX-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 description 1
- BZGLBXYQOMFXAU-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propyl 3,4-dichlorobenzoate Chemical compound CC1CCCCN1CCCOC(=O)C1=CC=C(Cl)C(Cl)=C1 BZGLBXYQOMFXAU-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RKNCIBMWPVZEAJ-UHFFFAOYSA-N 3-bromoprop-1-ynylbenzene Chemical compound BrCC#CC1=CC=CC=C1 RKNCIBMWPVZEAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- BZAHCTXWHBGSRK-UHFFFAOYSA-N 4,5-dichloro-6-(1-fluoroethyl)pyrimidine Chemical compound CC(F)C1=NC=NC(Cl)=C1Cl BZAHCTXWHBGSRK-UHFFFAOYSA-N 0.000 description 1
- NUEYDUKUIXVKNB-UHFFFAOYSA-N 4,6-dichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=CN=C1Cl NUEYDUKUIXVKNB-UHFFFAOYSA-N 0.000 description 1
- HCTISZQLTGAYOX-UHFFFAOYSA-N 4,6-dichloro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(Cl)N=CN=C1Cl HCTISZQLTGAYOX-UHFFFAOYSA-N 0.000 description 1
- NYEOKRVTIYIBGF-UHFFFAOYSA-N 4,6-dichloro-5-phenylpyrimidine Chemical compound ClC1=NC=NC(Cl)=C1C1=CC=CC=C1 NYEOKRVTIYIBGF-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
- MQBDOJQCVCCAAH-UHFFFAOYSA-N 4-(1,3-thiazol-2-yl)but-3-yn-1-amine Chemical compound NCCC#CC1=NC=CS1 MQBDOJQCVCCAAH-UHFFFAOYSA-N 0.000 description 1
- RVLXZMAMUZQMCK-UHFFFAOYSA-N 4-(2-benzyl-1,3-thiazol-4-yl)but-3-yn-1-amine Chemical compound NCCC#CC1=CSC(CC=2C=CC=CC=2)=N1 RVLXZMAMUZQMCK-UHFFFAOYSA-N 0.000 description 1
- OKSOXYMFHGHTSO-UHFFFAOYSA-N 4-(2-phenoxy-1,3-thiazol-4-yl)but-3-yn-1-amine Chemical compound NCCC#CC1=CSC(OC=2C=CC=CC=2)=N1 OKSOXYMFHGHTSO-UHFFFAOYSA-N 0.000 description 1
- MYMYUBKWCXJECN-UHFFFAOYSA-N 4-(2-phenyl-1,3-thiazol-4-yl)but-3-yn-1-amine Chemical compound NCCC#CC1=CSC(C=2C=CC=CC=2)=N1 MYMYUBKWCXJECN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 1
- VDTIGYKLTROQAH-UHFFFAOYSA-N 4-bromo-1,3-thiazole Chemical compound BrC1=CSC=N1 VDTIGYKLTROQAH-UHFFFAOYSA-N 0.000 description 1
- YJESUUGBCWVUTC-UHFFFAOYSA-N 4-bromo-2-phenoxy-1,3-thiazole Chemical compound BrC1=CSC(OC=2C=CC=CC=2)=N1 YJESUUGBCWVUTC-UHFFFAOYSA-N 0.000 description 1
- QHQLARFUTJXZOQ-UHFFFAOYSA-N 4-chloro-6-(1-fluoroethyl)-5-iodopyrimidine Chemical compound CC(F)C1=NC=NC(Cl)=C1I QHQLARFUTJXZOQ-UHFFFAOYSA-N 0.000 description 1
- MVAXKFAQKTWRAH-UHFFFAOYSA-N 4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC=N1 MVAXKFAQKTWRAH-UHFFFAOYSA-N 0.000 description 1
- IYJDOVYAFDVIDB-UHFFFAOYSA-N 4-chloro-7-methylthieno[3,2-d]pyrimidine Chemical compound N1=CN=C2C(C)=CSC2=C1Cl IYJDOVYAFDVIDB-UHFFFAOYSA-N 0.000 description 1
- BPTCCCTWWAUJRK-UHFFFAOYSA-N 4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CN2 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 1
- MBFHUWCOCCICOK-UHFFFAOYSA-N 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(I)C=2)C(O)=O)=N1 MBFHUWCOCCICOK-UHFFFAOYSA-N 0.000 description 1
- OXRWICUICBZVAE-UHFFFAOYSA-N 4-methylpent-1-yne Chemical compound CC(C)CC#C OXRWICUICBZVAE-UHFFFAOYSA-N 0.000 description 1
- SVYBVQAVNRJJQZ-UHFFFAOYSA-N 4-phenyl-2-[(quinazolin-4-ylamino)methyl]but-3-yn-1-ol Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(CO)C#CC1=CC=CC=C1 SVYBVQAVNRJJQZ-UHFFFAOYSA-N 0.000 description 1
- VICFISWUVIINPR-UHFFFAOYSA-N 4-phenylbut-3-yn-1-amine Chemical compound NCCC#CC1=CC=CC=C1 VICFISWUVIINPR-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- PMOCSIGHRYWEGB-UHFFFAOYSA-N 4-trimethylsilylbut-3-yn-1-amine Chemical compound C[Si](C)(C)C#CCCN PMOCSIGHRYWEGB-UHFFFAOYSA-N 0.000 description 1
- NUZOPJSNULIDTB-UHFFFAOYSA-N 4-trimethylsilylbut-3-ynyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC#C[Si](C)(C)C)C=C1 NUZOPJSNULIDTB-UHFFFAOYSA-N 0.000 description 1
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- AIEIYOQMLDXJFT-UHFFFAOYSA-N 5-phenylpent-4-yn-2-amine Chemical compound CC(N)CC#CC1=CC=CC=C1 AIEIYOQMLDXJFT-UHFFFAOYSA-N 0.000 description 1
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h 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](C(C)C)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.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
- DPIYFSYESCKFBK-UHFFFAOYSA-N 6-methylhept-3-yn-1-amine Chemical compound CC(C)CC#CCCN DPIYFSYESCKFBK-UHFFFAOYSA-N 0.000 description 1
- UEFRUCZXPDBXSV-UHFFFAOYSA-N 6-methylhept-3-yn-1-ol Chemical compound CC(C)CC#CCCO UEFRUCZXPDBXSV-UHFFFAOYSA-N 0.000 description 1
- HVUBXNQWXJBVHB-SQFISAMPSA-N 7Z-Eicosen-11-one Chemical compound CCCCCCCCCC(=O)CC\C=C/CCCCCC HVUBXNQWXJBVHB-SQFISAMPSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GSAAJQNJNPBBSX-WAYWQWQTSA-N 9Z-Tetradecen-1-ol Chemical compound CCCC\C=C/CCCCCCCCO GSAAJQNJNPBBSX-WAYWQWQTSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 241000328088 Acaudaleyrodes rachipora Species 0.000 description 1
- 241001558877 Aceria tulipae Species 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000515126 Acusta despecta sieboldiana Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 241000212251 Alternaria dauci Species 0.000 description 1
- 241000352690 Alternaria kikuchiana Species 0.000 description 1
- 241000266345 Alternaria radicina Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241001558165 Alternaria sp. Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- 239000005727 Amisulbrom Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000673723 Ampelophaga Species 0.000 description 1
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001463392 Anoplophora macularia Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000276082 Apethymus Species 0.000 description 1
- 241001312832 Aphidius colemani Species 0.000 description 1
- 241000372435 Aphidoletes aphidimyza Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241000256837 Apidae Species 0.000 description 1
- 241001503479 Athalia Species 0.000 description 1
- 241000902805 Aulacophora Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241001367035 Autographa nigrisigna Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 239000005469 Azimsulfuron Substances 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 239000005736 Benthiavalicarb Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000005653 Bifenazate Substances 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 1
- 239000005740 Boscalid Substances 0.000 description 1
- 241000555706 Botryosphaeria dothidea Species 0.000 description 1
- 241000499339 Botrytis allii Species 0.000 description 1
- 241000322476 Bovicola bovis Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 239000005742 Bupirimate Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 1
- SOFLUGHCCPJMGI-UHFFFAOYSA-N C(=C)C(CN1C(C2=CC=CC=C2C1=O)=O)C#CC1=CC=CC=C1.C(=C)C(CN)C#CC1=CC=CC=C1 Chemical compound C(=C)C(CN1C(C2=CC=CC=C2C1=O)=O)C#CC1=CC=CC=C1.C(=C)C(CN)C#CC1=CC=CC=C1 SOFLUGHCCPJMGI-UHFFFAOYSA-N 0.000 description 1
- JKUVBJKYBKWWLY-UHFFFAOYSA-N C(CCCCCCCCCC=C/CC)CC(=O)O.C(C)(=O)O Chemical compound C(CCCCCCCCCC=C/CC)CC(=O)O.C(C)(=O)O JKUVBJKYBKWWLY-UHFFFAOYSA-N 0.000 description 1
- SOWONIUWEXBIQZ-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)C=1SC=C(N1)Br Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)C=1SC=C(N1)Br SOWONIUWEXBIQZ-UHFFFAOYSA-N 0.000 description 1
- JTQQJTFHMQQNSA-UHFFFAOYSA-N CN(C=O)C.C[Si](C#CCCN1C(C2=CC=CC=C2C1=O)=O)(C)C Chemical compound CN(C=O)C.C[Si](C#CCCN1C(C2=CC=CC=C2C1=O)=O)(C)C JTQQJTFHMQQNSA-UHFFFAOYSA-N 0.000 description 1
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
- 241001182720 Cacopsylla pyrisuga Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004343 Calcium peroxide Substances 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 241001660166 Camponotus japonicus Species 0.000 description 1
- 241000346816 Capnodium salicinum Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000005490 Carbetamide Substances 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000003801 Castanea crenata Nutrition 0.000 description 1
- 244000209117 Castanea crenata Species 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000338134 Cercospora asparagi Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 241001658057 Cercospora kikuchii Species 0.000 description 1
- 241001450756 Ceroplastes rubens Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005887 Chromafenozide Substances 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241000688200 Cingulata Species 0.000 description 1
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 1
- 241001498622 Cixius wagneri Species 0.000 description 1
- 241000137094 Cladosporium allicinum Species 0.000 description 1
- 241000317965 Cladosporium allii-cepae Species 0.000 description 1
- 241001149956 Cladosporium herbarum Species 0.000 description 1
- 239000005654 Clofentezine Substances 0.000 description 1
- 239000005888 Clothianidin Substances 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- CSWBSLXBXRFNST-UHFFFAOYSA-N Codlemone Natural products CC=CC=CCCCCCCCO CSWBSLXBXRFNST-UHFFFAOYSA-N 0.000 description 1
- 241001123536 Colletotrichum acutatum Species 0.000 description 1
- 241000570797 Colletotrichum carthami Species 0.000 description 1
- 241001046921 Colletotrichum chrysanthemi Species 0.000 description 1
- 241001600676 Colletotrichum higginsianum Species 0.000 description 1
- 241000152100 Colletotrichum horii Species 0.000 description 1
- 241001306229 Colletotrichum spinaciae Species 0.000 description 1
- 239000005752 Copper oxychloride Substances 0.000 description 1
- 241001509962 Coptotermes formosanus Species 0.000 description 1
- 241000248757 Cordyceps brongniartii Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000258924 Ctenocephalides felis Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 239000005754 Cyazofamid Substances 0.000 description 1
- 241000612153 Cyclamen Species 0.000 description 1
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 description 1
- 239000005755 Cyflufenamid Substances 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- 241001609607 Delia platura Species 0.000 description 1
- 239000005503 Desmedipham Substances 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241001306390 Diaporthe ampelina Species 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- 241001273467 Didymella pinodes Species 0.000 description 1
- 239000005759 Diethofencarb Substances 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- DHWRNDJOGMTCPB-UHFFFAOYSA-N Dimefuron Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1C(=O)OC(C(C)(C)C)=N1 DHWRNDJOGMTCPB-UHFFFAOYSA-N 0.000 description 1
- IKYICRRUVNIHPP-UHFFFAOYSA-N Dimethametryn Chemical compound CCNC1=NC(NC(C)C(C)C)=NC(SC)=N1 IKYICRRUVNIHPP-UHFFFAOYSA-N 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- 241001523339 Discula theae-sinensis Species 0.000 description 1
- 239000005764 Dithianon Substances 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 241001446133 Drosicha corpulenta Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241001566624 Eciton Species 0.000 description 1
- 241001566614 Eciton burchellii Species 0.000 description 1
- 241000901048 Elsinoe ampelina Species 0.000 description 1
- 241000125118 Elsinoe fawcettii Species 0.000 description 1
- 241001222563 Empoasca onukii Species 0.000 description 1
- 206010014970 Ephelides Diseases 0.000 description 1
- 241001555556 Ephestia elutella Species 0.000 description 1
- 241001518474 Epiacanthus Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- 241000260853 Epuraea terminalis Species 0.000 description 1
- 241000029125 Erysiphe alphitoides Species 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000005976 Ethephon Substances 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 description 1
- 239000005896 Etofenprox Substances 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- 241000020674 Euhadra peliomphala Species 0.000 description 1
- 241000659205 Eysarcoris ventralis Species 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- 239000005776 Fenhexamid Substances 0.000 description 1
- 239000005898 Fenoxycarb Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005900 Flonicamid Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005901 Flubendiamide Substances 0.000 description 1
- 239000005531 Flufenacet Substances 0.000 description 1
- 239000005782 Fluopicolide Substances 0.000 description 1
- 239000005783 Fluopyram Substances 0.000 description 1
- 239000005559 Flurtamone Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 239000005560 Foramsulfuron Substances 0.000 description 1
- 239000005790 Fosetyl Substances 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223197 Fusarium lateritium Species 0.000 description 1
- 241000611205 Fusarium oxysporum f. sp. lycopersici Species 0.000 description 1
- 241000879842 Fusarium oxysporum f. sp. melonis Species 0.000 description 1
- 241000489964 Fusicladium Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 241001620302 Glomerella <beetle> Species 0.000 description 1
- 241000694578 Glomerella sp. (in: Fungi) Species 0.000 description 1
- 241000257334 Glossina palpalis Species 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000532524 Grovesinia pyramidalis Species 0.000 description 1
- 241001194823 Gymnosporangium asiaticum Species 0.000 description 1
- 241000179420 Haemaphysalis longicornis Species 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241000825556 Halyomorpha halys Species 0.000 description 1
- 241001147381 Helicoverpa armigera Species 0.000 description 1
- 241000510199 Helicoverpa assulta Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241001581044 Hellula undalis Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000005794 Hymexazol Substances 0.000 description 1
- 241000543830 Hypoderma bovis Species 0.000 description 1
- 241000257174 Hypoderma lineatum Species 0.000 description 1
- 241001058150 Icerya purchasi Species 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- FKWDSATZSMJRLC-UHFFFAOYSA-N Iminoctadine acetate Chemical compound CC([O-])=O.CC([O-])=O.CC([O-])=O.NC([NH3+])=NCCCCCCCC[NH2+]CCCCCCCCN=C(N)[NH3+] FKWDSATZSMJRLC-UHFFFAOYSA-N 0.000 description 1
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 description 1
- 239000005907 Indoxacarb Substances 0.000 description 1
- 239000005568 Iodosulfuron Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- 241000188153 Isaria fumosorosea Species 0.000 description 1
- 239000005908 Isaria fumosorosea Apopka strain 97 (formely Paecilomyces fumosoroseus) Substances 0.000 description 1
- 239000005571 Isoxaflutole Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005800 Kresoxim-methyl Substances 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- 239000005717 Laminarin Substances 0.000 description 1
- 229920001543 Laminarin Polymers 0.000 description 1
- 240000006568 Lathyrus odoratus Species 0.000 description 1
- 241001261797 Leptoconops Species 0.000 description 1
- 241000284249 Leptocorisa chinensis Species 0.000 description 1
- 241000896221 Leveillula taurica Species 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 241000594033 Liriomyza bryoniae Species 0.000 description 1
- 241001520143 Liriomyza trifolii Species 0.000 description 1
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
- 241000012186 Litura Species 0.000 description 1
- 239000005912 Lufenuron Substances 0.000 description 1
- 241001190650 Lyonetia prunifoliella Species 0.000 description 1
- 241001547796 Macrophoma Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 241001646125 Mandarina Species 0.000 description 1
- 239000005804 Mandipropamid Substances 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 241000330845 Marssonina coronariae Species 0.000 description 1
- 241001422926 Mayetiola hordei Species 0.000 description 1
- 241001318725 Meghimatium bilineatum Species 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 241000243787 Meloidogyne hapla Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000292449 Menacanthus stramineus Species 0.000 description 1
- 239000005806 Meptyldinocap Substances 0.000 description 1
- 239000005577 Mesosulfuron Substances 0.000 description 1
- 239000005914 Metaflumizone Substances 0.000 description 1
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 description 1
- 239000005808 Metalaxyl-M Substances 0.000 description 1
- 239000005579 Metamitron Substances 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- 239000005951 Methiocarb Substances 0.000 description 1
- 239000005917 Methoxyfenozide Substances 0.000 description 1
- 239000005809 Metiram Substances 0.000 description 1
- 239000005582 Metosulam Substances 0.000 description 1
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 1
- 239000005810 Metrafenone Substances 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- 241001625791 Microxyphium Species 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- 241001518836 Monilinia fructigena Species 0.000 description 1
- 241000862466 Monilinia laxa Species 0.000 description 1
- 241000351915 Monochaetia monochaeta Species 0.000 description 1
- 241001442207 Monochamus alternatus Species 0.000 description 1
- 241001190694 Muda Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000238367 Mya arenaria Species 0.000 description 1
- FTCOKXNKPOUEFH-UHFFFAOYSA-N Myclozolin Chemical compound O=C1C(COC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FTCOKXNKPOUEFH-UHFFFAOYSA-N 0.000 description 1
- 244000309595 Mycosphaerella horii Species 0.000 description 1
- 241001433116 Mycosphaerella nawae Species 0.000 description 1
- 241000736258 Myrmecia <insect> Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 1
- IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 description 1
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 description 1
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 description 1
- 239000005585 Napropamide Substances 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- 241001658757 Neoseiulus californicus Species 0.000 description 1
- 241001455175 Neoseiulus cucumeris Species 0.000 description 1
- 241000359016 Nephotettix Species 0.000 description 1
- 241001671709 Nezara viridula Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000866536 Odontotermes formosanus Species 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241001012098 Omiodes indicata Species 0.000 description 1
- 241001635524 Orius strigicollis Species 0.000 description 1
- 241000346285 Ostrinia furnacalis Species 0.000 description 1
- 241001570894 Oulema oryzae Species 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241000497111 Paralobesia viteana Species 0.000 description 1
- 241001622642 Parnara bada Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000588701 Pectobacterium carotovorum Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 241001510010 Periplaneta fuliginosa Species 0.000 description 1
- 241000048273 Periplaneta japonica Species 0.000 description 1
- 241000118319 Peronospora effusa Species 0.000 description 1
- 241000172292 Pestalotiopsis diospyri Species 0.000 description 1
- 241000682645 Phakopsora pachyrhizi Species 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- 241001480007 Phomopsis Species 0.000 description 1
- 241001645346 Phomopsis asparagi Species 0.000 description 1
- 241000579813 Phyllactinia Species 0.000 description 1
- 241000519856 Phyllosticta Species 0.000 description 1
- 241000210649 Phyllosticta ampelicida Species 0.000 description 1
- 241001396980 Phytonemus pallidus Species 0.000 description 1
- 241000233631 Phytophthora citrophthora Species 0.000 description 1
- 241000233620 Phytophthora cryptogea Species 0.000 description 1
- 241000948156 Phytophthora syringae Species 0.000 description 1
- 241000179203 Phytoseiulus persimilis Species 0.000 description 1
- 241000227425 Pieris rapae crucivora Species 0.000 description 1
- 241000691880 Planococcus citri Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000896242 Podosphaera Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241001294742 Podosphaera macularis Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 239000005601 Propoxycarbazone Substances 0.000 description 1
- 241000736232 Prosimulium Species 0.000 description 1
- 239000005603 Prosulfocarb Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 241000899394 Pseudocercospora Species 0.000 description 1
- 241000301598 Pseudocercospora kaki Species 0.000 description 1
- 241000386899 Pseudocercospora vitis Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000990000 Puccinia cnici-oleracei Species 0.000 description 1
- 239000005925 Pymetrozine Substances 0.000 description 1
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 1
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005926 Pyridalyl Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- 241000342339 Pythium ultimum var. ultimum Species 0.000 description 1
- 239000005831 Quinoxyfen Substances 0.000 description 1
- 241001421802 Ramularia grevilleana Species 0.000 description 1
- 241000866500 Reticulitermes speratus Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241000260845 Rhizoglyphus robini Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 241000133716 Riptortus clavatus Species 0.000 description 1
- 241001299714 Rosellinia necatrix Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000253973 Schistocerca gregaria Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 241000113469 Septoria perillae Species 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 241000254154 Sitophilus zeamais Species 0.000 description 1
- 241000176086 Sogatella furcifera Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 241000227724 Sphaceloma Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 description 1
- 239000005929 Spinetoram Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 239000005665 Spiromesifen Substances 0.000 description 1
- 239000005931 Spirotetramat Substances 0.000 description 1
- 239000005837 Spiroxamine Substances 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001523414 Steinernema glaseri Species 0.000 description 1
- 241001529604 Steinernema kushidai Species 0.000 description 1
- 241000266365 Stemphylium vesicarium Species 0.000 description 1
- 241000346835 Stenella <ascomycete fungus> Species 0.000 description 1
- 241001508985 Stephanitis pyrioides Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000228343 Talaromyces flavus Species 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 239000005847 Triazoxide Substances 0.000 description 1
- 241000255985 Trichoplusia Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- 241000462092 Trioza erytreae Species 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 241000611866 Tyrophagus putrescentiae Species 0.000 description 1
- 241001630065 Unaspis yanonensis Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241001006642 Venturia pyrina Species 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000587986 Zasmidium citri-griseum Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000005870 Ziram Substances 0.000 description 1
- 239000005863 Zoxamide Substances 0.000 description 1
- 241001360088 Zymoseptoria tritici Species 0.000 description 1
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 description 1
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 description 1
- QEZHSXDSWBLPKD-UHFFFAOYSA-M [Br-].CC[Mg+].C1CCOC1 Chemical compound [Br-].CC[Mg+].C1CCOC1 QEZHSXDSWBLPKD-UHFFFAOYSA-M 0.000 description 1
- VEMHQNXVHVAHDN-UHFFFAOYSA-J [Cu+2].[Cu+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O Chemical compound [Cu+2].[Cu+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VEMHQNXVHVAHDN-UHFFFAOYSA-J 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- UELITFHSCLAHKR-UHFFFAOYSA-N acibenzolar-S-methyl Chemical group CSC(=O)C1=CC=CC2=C1SN=N2 UELITFHSCLAHKR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 1
- 229950000294 azaconazole Drugs 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 1
- ONHBDDJJTDTLIR-UHFFFAOYSA-N azocyclotin Chemical compound C1CCCCC1[Sn](N1N=CN=C1)(C1CCCCC1)C1CCCCC1 ONHBDDJJTDTLIR-UHFFFAOYSA-N 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- RHFIHMITVTUUFG-UHFFFAOYSA-M benzyl zinc bromide tetrahydrofuran Chemical compound [Zn+2].[Br-].C1CCOC1.[CH2-]C1=CC=CC=C1 RHFIHMITVTUUFG-UHFFFAOYSA-M 0.000 description 1
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- 230000000853 biopesticidal effect Effects 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 description 1
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 1
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- STOASOOVVADOKH-UHFFFAOYSA-N but-3-ynyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC#C)C=C1 STOASOOVVADOKH-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000019402 calcium peroxide Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 description 1
- 150000005698 chloropyrimidines Chemical class 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 1
- 229930186364 cyclamen Natural products 0.000 description 1
- GLWWLNJJJCTFMZ-UHFFFAOYSA-N cyclanilide Chemical compound C=1C=C(Cl)C=C(Cl)C=1NC(=O)C1(C(=O)O)CC1 GLWWLNJJJCTFMZ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 description 1
- 229950000775 cyromazine Drugs 0.000 description 1
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 description 1
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 1
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 1
- QUGJYNGNUBHTNS-UHFFFAOYSA-N ethyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OCC)C1=CC=CC=C1 QUGJYNGNUBHTNS-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 229950005085 etofenprox Drugs 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 1
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 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 1
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- GOWLARCWZRESHU-AQTBWJFISA-N ferimzone Chemical compound C=1C=CC=C(C)C=1C(/C)=N\NC1=NC(C)=CC(C)=N1 GOWLARCWZRESHU-AQTBWJFISA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 description 1
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
- 229960004884 fluconazole Drugs 0.000 description 1
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 description 1
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- GNVDAZSPJWCIQZ-UHFFFAOYSA-N flusulfamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GNVDAZSPJWCIQZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 description 1
- 239000003501 hydroponics Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- 229940088649 isoxaflutole Drugs 0.000 description 1
- 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 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 229930001540 kinoprene Natural products 0.000 description 1
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical group CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- BYRPTKZOXNFFDB-UHFFFAOYSA-N lithium;bis(trimethylsilyl)azanide;oxolane Chemical compound [Li+].C1CCOC1.C[Si](C)(C)[N-][Si](C)(C)C BYRPTKZOXNFFDB-UHFFFAOYSA-N 0.000 description 1
- 241000238565 lobster Species 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IXJOSTZEBSTPAG-UHFFFAOYSA-N methasulfocarb Chemical compound CNC(=O)SC1=CC=C(OS(C)(=O)=O)C=C1 IXJOSTZEBSTPAG-UHFFFAOYSA-N 0.000 description 1
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 229920000257 metiram Polymers 0.000 description 1
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- NDFQJIDTWQPCEC-UHFFFAOYSA-N n-(1,4-diphenylbut-3-ynyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C=1C=CC=CC=1)CC#CC1=CC=CC=C1 NDFQJIDTWQPCEC-UHFFFAOYSA-N 0.000 description 1
- QAECCHUZCKOYON-UHFFFAOYSA-N n-(4-phenylbut-3-ynyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NCCC#CC1=CC=CC=C1 QAECCHUZCKOYON-UHFFFAOYSA-N 0.000 description 1
- JPUMCICZUJKOJC-UHFFFAOYSA-N n-(5-phenylpent-4-yn-2-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NC(C)CC#CC1=CC=CC=C1 JPUMCICZUJKOJC-UHFFFAOYSA-N 0.000 description 1
- BZTSGFSFZIUTSZ-UHFFFAOYSA-N n-(6-methylhept-3-ynyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound CC(C)CC#CCCNC1=NC=NC2=C1C=CS2 BZTSGFSFZIUTSZ-UHFFFAOYSA-N 0.000 description 1
- BOLJYEVOEGYLKA-UHFFFAOYSA-N n-[2-(2-phenylethynyl)but-3-enyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C=C)C#CC1=CC=CC=C1 BOLJYEVOEGYLKA-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- QHTKXSKYVVHKOD-UHFFFAOYSA-N n-[4-(1,3-thiazol-2-yl)but-3-ynyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NCCC#CC1=NC=CS1 QHTKXSKYVVHKOD-UHFFFAOYSA-N 0.000 description 1
- HFAHLTXPFMHJFG-UHFFFAOYSA-N n-[4-(2-benzyl-1,3-thiazol-4-yl)but-3-ynyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NCCC#CC(N=1)=CSC=1CC1=CC=CC=C1 HFAHLTXPFMHJFG-UHFFFAOYSA-N 0.000 description 1
- FQDPOCINDCWCKQ-UHFFFAOYSA-N n-[4-(2-phenoxy-1,3-thiazol-4-yl)but-3-ynyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NCCC#CC(N=1)=CSC=1OC1=CC=CC=C1 FQDPOCINDCWCKQ-UHFFFAOYSA-N 0.000 description 1
- PCCMWPAVINTXEW-UHFFFAOYSA-N n-[4-(2-phenyl-1,3-thiazol-4-yl)but-3-ynyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=CC=2C=1NCCC#CC(N=1)=CSC=1C1=CC=CC=C1 PCCMWPAVINTXEW-UHFFFAOYSA-N 0.000 description 1
- HFEDNVVLUNBXAM-UHFFFAOYSA-N n-but-3-ynylthieno[2,3-d]pyrimidin-4-amine Chemical compound C#CCCNC1=NC=NC2=C1C=CS2 HFEDNVVLUNBXAM-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- FYRQBVQDBVDHHB-UHFFFAOYSA-N n-methyl-4-phenyl-2-[(quinazolin-4-ylamino)methyl]but-3-ynamide Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C(=O)NC)C#CC1=CC=CC=C1 FYRQBVQDBVDHHB-UHFFFAOYSA-N 0.000 description 1
- LLLILZLFKGJCCV-UHFFFAOYSA-M n-methyl-n-[(1-methylpyridin-1-ium-4-yl)methylideneamino]aniline;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1N(C)\N=C\C1=CC=[N+](C)C=C1 LLLILZLFKGJCCV-UHFFFAOYSA-M 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- GAGSAAHZRBTRGD-UHFFFAOYSA-N oxirane;oxolane Chemical compound C1CO1.C1CCOC1 GAGSAAHZRBTRGD-UHFFFAOYSA-N 0.000 description 1
- YWWARDMVSMPOLR-UHFFFAOYSA-M oxolane;tetrabutylazanium;fluoride Chemical compound [F-].C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC YWWARDMVSMPOLR-UHFFFAOYSA-M 0.000 description 1
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
- JTHLRRZARWSHBE-UHFFFAOYSA-N pent-4-yn-2-ol Chemical compound CC(O)CC#C JTHLRRZARWSHBE-UHFFFAOYSA-N 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229930185156 spinosyn Natural products 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- 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
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-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
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical group N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 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
- 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
- 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
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-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
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Hematology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0〜3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
b)炭素原子数1〜6個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニル、炭素原子数3〜8個のシクロアルキルまたは炭素原子数3〜8個のシクロアルケニル、
c)−SiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、
d)水素原子
から選択され、a)b)の場合、R1は−C(O)OR、−C(O)R、−R、−OR、−SR、−SO2R、−OC(O)R、−C(O)NHR、−C(O)NR2、−NHSO2R、−NRSO2R、−NHR、−NR2、−NHC(O)R、−NRC(O)R、−NHC(O)OR、−NRC(O)OR、−N(OR)C(O)OR、−NHSO2R、−NRSO2R、−SO2NHR、−SO2NR2(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、−SiR5R6R7、−OSiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、ハロアルキル(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のアルキル基)、ハロアルケニル(同一又は異なって、ハロゲン原子1〜4で置換されている炭素原子数が2〜6の直鎖状又は分岐状のアルケニル基)、ハロアルコキシ(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のアルコキシ基)、アシルアルコキシ((炭素原子数が1〜8の直鎖状又は分岐状の脂肪族炭化水素基)−CO−で表されるアシル基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルコキシ基)、アシルオキシアルキル((炭素原子数が1〜8の直鎖状又は分岐状の脂肪族炭化水素基)−CO−O−で表されるアシルオキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、アルキルスルホニルアルキル(炭素原子数が1〜8の直鎖状又は分岐状のアルキルスルホニル基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、シロキシアルキル(−OSiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、ヒドロキシアルキル(ヒドロキシル基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、アルコキシアルキル(炭素原子数が1〜8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、ハロアルコキシアルキル(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のハロアルコキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、アルキルチオアルキル(炭素原子数が1〜8の直鎖状又は分岐状のアルキルチオ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、ジアルコキシアセタール(炭素原子数が1〜8の直鎖状又は分岐状のアルコキシ基がメチル基に2個置換したジアルコキシメチル基)、アルコキシアルコキシ(炭素原子数が1〜8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、シアノアルキル(シアノ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾジオキソリル、イミド、ホルミル(−CHO)、カルボキシル(−COOH)、ホルムアミド(−NHCHO)、環状エーテル、および環状アミンで置換されていてもよく、
R2は水素原子、−R、−OR、−C(O)OR、−C(O)NHR、−CONR2(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、ヒドロキシアルキル(ヒドロキシル基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、アルコキシアルキル(炭素原子数が1〜8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、ハロアルコキシアルキル(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のハロアルコキシ基により置換された炭素原子数1〜3の直鎖状又は分岐状のアルキル基)、フェニル、ヘテロアリール、ハロゲン、シアノ、ハロアルキル(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のアルキル基)、ハロアルコキシ(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のアルコキシ基)を表し、
R3は(1)水素原子、(2)ハロゲン原子、(3)(炭素原子数1〜8個の直鎖状又は分岐状の脂肪族炭化水素基)−CO−O−で表されるアシルオキシ、ハロゲン原子若しくは水酸基で置換された炭素原子数1〜6個のアルキル、(4)無置換の炭素原子数1〜6個のアルキル、(5)−OR、−SR、−SO2R(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、または(6)ハロアルキル(同一又は異なって、ハロゲン原子1〜9で置換されている炭素原子数が1〜4の直鎖状又は分岐状のアルキル基)を表し、
R4は水素原子、ハロゲン原子、炭素原子数1〜6個のアルキル、ニトロ、アミノ、フェニル、ベンジル又はR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表す。]
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0〜3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環を構成する任意の環原子(炭素原子またはヘテロ原子)を結合手とする基。
b)炭素原子数1〜6個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニル、炭素原子数3〜8個のシクロアルキルまたは炭素原子数3〜8個のシクロアルケニル。
c)−SiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが違う置換基でもよい)。
d)水素原子。
を挙げることができるが、R8が水素原子若しくは塩素原子であるチエノ[2,3−d]ピリミジン環が好ましい。
を挙げることができるが、R8が水素原子、フッ素原子若しくは塩素原子であるキナゾリン環が好ましい。
N−(3−ブチニル)フタルイミド誘導体[VIII]とヨウ化若しくは臭化フェニル、ヨウ化、臭化若しくは塩化へテロアリール、ヨウ化若しくは臭化アルケニル[V]で薗頭反応を行った後、生成物[IX]をヒドラジン(hydrazine)若しくは塩基により脱保護することにより3−ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール[X]とフタルイミド[XI]から光延反応(Mitsunobu reaction)により生成物[XII]を合成し、生成物[XII]を合成法1と同様、薗頭反応、脱保護を行うことにより3−ブチニルアミン誘導体[III]を製造できる。
末端アルキン[XII]をグリニヤール試薬と反応後、さらにエチレンオキシド[XIII]と反応させて3−ブチニルアルコール誘導体[XIV]を合成する。その後、このアルコールを光延反応、脱保護を行うことにより3−ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール(X)をトシル基で保護した後、アルキルリチウムにより末端アルキン炭素にアニオンを発生させ、求核置換反応により末端アルキン炭素に置換基を導入し生成物[XVI]を製造する。その後、ヨウ化カリウム存在下、カリウムフタルイミド[XVII]と反応させ、生成物[IX]を得る。その後、脱保護を行うことにより3−ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール[XIV]をトシル基で保護した化合物[XVIII]にアジ化ナトリウムを反応させて、アジド化合物[XIV]を製造する。その後、このアジド化合物[XIV]を水素化アルミニウムリチウムで還元する事により、3−ブチニルアミン誘導体[III]を製造できる。
4−ペンチルアミド[XX]からHofmann転移により、3−ブチニルアミン誘導体[III]を製造できる。
アジ化アシル[XXI]からCurtius転移により、3−ブチニルアミン誘導体[III]を製造できる。
本願発明において、「有害生物」という用語は、農園芸用植物に対するあらゆる病害虫及び農園芸用植物に対するあらゆる病原菌を包含する。
本発明の農園芸用の有害生物防除剤は、特に、殺菌効果および殺虫効果が顕著であり、式[I]で示される化合物の1種若しくは2種以上を有効成分として含有するものである。
(1)一般式(I)においてR1=TMS(トリメチルシリル),R2=H,R3−R4=チオフェン(表1、化合物No.2の合成)
段階A:3−ブチニル p−トルエンスルホネート
ジクロロメタン500mlに3−ブチン−1−オール10.00g、トリエチルアミン40mlを加えて溶液を0℃に冷却した。その溶液にパラトルエンスルホニルクロリド30.00gをゆっくり加え、その後室温で一晩撹拌後、反応液に水を加え、ジクロロメタン200mlで2回抽出した。有機層を2回水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、ヘキサン:酢酸エチル=6:1)で精製することによってO−トシル化合物13.52gを得た。
段階B:4−トリメチルシラニル−3−ブチニル p−トルエンスルホネート
窒素置換したフラスコに乾燥テトラヒドロフラン130ml、上記段階で得られたO−トシル化合物6.45gを加え、溶液を−78℃に冷却した。冷却後この溶液に1.6Mのn−ブチルリチウムヘキサン溶液18.9mlをゆっくりと滴下した。滴下後−78℃で溶液を2時間撹拌し、トリメチルシリルクロリド5.5mlをゆっくりと滴下した。滴下後−78℃で溶液を15分間撹拌し、さらに室温で1時間撹拌した。撹拌後反応液に水150mlを加え、ジクロロメタン150mlで2回抽出後、硫酸マグネシウムで乾燥した。有機層を濃縮し、残渣を真空下乾燥させる事でトリメチルシリル化合物8.37gを得た。
段階C:2−(4−トリメチルシラニル−3−ブチニル)イソインドール−1,3−ジオン
N,N−ジメチルホルムアミド64mlに上記段階で得られたトリメチルシリル化合物8.37g、フタルイミドカリウム7.85g、ヨウ化カリウム0.46gを加え、140℃で2時間撹拌した。室温まで冷却後、反応液に水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、飽和食塩水100mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによってフタルイミド化合物3.28gを得た。
段階D:4−トリメチルシラニル−3−ブチニルアミン
上記段階で得られたフタルイミド化合物3.28gにメタノール121ml、ヒドラジン一水和物(80%)2.25gを加え、一晩撹拌した。反応液を濃縮し、残渣をクロロホルム50mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.72gを得た。
段階E:4−(4−トリメチルシラニル−3−ブチニルアミノ)チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド32mlに上記段階で得られたアミン1.72g、4−クロロチエノ[2,3−d]ピリミジン1.72g、トリエチルアミン1.7mlを加え、80℃で4時間撹拌した。反応液を冷却後、水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水50mlで2回、さらに飽和食塩水50mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物1.83gを得た。
同様の製造法により、表1、化合物No.3〜5、87を合成した。
窒素置換したフラスコにテトラヒドロフラン16ml、(1)で得られた4−(4−トリメチルシラニル−3−ブチニルアミノ)チエノ[2,3−d]ピリミジン0.37g、1Mのテトラブチルアンモニウムフルオライドテトラヒドロフラン溶液2.1mlを加え、室温で5時間撹拌した。撹拌後、反応液に飽和塩化アンモニウム水溶液50mlを加え、ジクロロメタン30mlで2回抽出した。有機層を飽和食塩水30mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって4−(3−ブチニルアミノ)チエノ[2,3−d]ピリミジン0.20gを得た。
同様の製造法により、表1、化合物No.86を合成した。
段階A:6−メチル−3−ヘプチン−1−オール
窒素置換したフラスコに乾燥テトラヒドロフラン22ml、1Mのエチルマグネシウムブロミドテトラヒドロフラン溶液25mlを加え、この溶液に4−メチルペンチン2.9mlをゆっくりと滴下した。この溶液を1時間室温で撹拌し、室温下で1.1Mのエチレンオキシドテトラヒドロフラン溶液25mlをゆっくり滴下し、さらに室温で一晩撹拌した。この反応液に飽和塩化アンモニウム水溶液100mlを加え、ジエチルエーテル100mlで2回抽出し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、生成したアルコールはそのまま次の反応に使用した(収量3.78g)。
段階B:2−(6−メチル−3−ヘプチニル)イソインドール−1,3−ジオン
窒素置換したフラスコに乾燥テトラヒドロフラン168ml、上記段階で得られたアルコール3.78g、フタルイミド4.06g、トリフェニルホスフィン7.21gを加え、この溶液に室温下でジエチルアゾジカルボキシレート(40%トルエン溶液)13.9mlをゆっくり滴下し、そのまま室温で1日撹拌した。反応液を濃縮後、残渣に水200mlを加え酢酸エチル150mlで2回抽出した。有機層を水200ml及び飽和食塩水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン)で精製することによってフタルイミド化合物5.08gを得た。
段階C:6−メチル−3−ヘプチニルアミン
上記段階で得られたフタルイミド化合物5.08gにメタノール200ml、ヒドラジン一水和物(80%)3.73gを加え、一晩撹拌した。反応液を濃縮し、残渣をクロロホルム50mlで洗浄し、洗浄したクロロホルムに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.65gを得た。
段階D:4−(6−メチル−3−ヘプチニルアミノ)チエノ[2,3−d]ピリミジン
DMF42mlに上記段階で得られたアミン1.65g、4−クロロチエノ[2,3−d]ピリミジン2.13g、トリエチルアミン1.9mlを加え、85℃で4時間撹拌した。反応液を冷却後、水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、さらに飽和食塩水100mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物2.14gを得た。
同様の製造法により、表1、化合物No.6,8,9,88〜91,94を合成した。
段階A:2−(4−フェニル−3−ブチニル)イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム535mg、ヨウ化銅145mg、N−(3−ブチニル)フタルイミド3.00gに窒素雰囲気下、テトラヒドロフラン35ml、ヨードベンゼン3.06g、トリエチルアミン9.0mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって、フタルイミド化合物3.70gを得た。
段階B:4−フェニル−3−ブチニルアミン
上記段階で得られたフタルイミド化合物3.70gにメタノール135ml、ヒドラジン一水和物(80%)2.52gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム50mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.94gを得た。
段階C:4−(4−フェニル−3−ブチニルアミノ)チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド31mlに上記段階で得られたアミン1.94g、4−クロロチエノ[2,3−d]ピリミジン1.90g、トリエチルアミン1.9mlを加え、85℃で4時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物1.68gを得た。
同様の製造法により、表1、化合物No.11〜28,32〜54,64〜67,84,85,96〜100,102〜126,128,130〜209,211〜214,306〜342,355〜380を合成した。
段階A:2−(1−メチル−3−ブチニル)イソインドール−1,3−ジオン
窒素置換したフラスコに乾燥テトラヒドロフラン400ml、4−ペンチン−2−オール5.00g、フタルイミド9.65g、トリフェニルホスフィン17.13gを加え、この溶液に室温下でジエチルアゾジカルボキシレート(40%トルエン溶液)30mlをゆっくり滴下し、そのまま室温で1日撹拌した。反応液を濃縮後、残渣に水300mlを加え酢酸エチル250mlで2回抽出した。有機層は水200ml及び飽和食塩水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン)で精製することによってフタルイミド化合物2.20gを得た。
段階B:2−(1−メチル−4−フェニル−3−ブチニル)イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム367mg、ヨウ化銅100mg、上記段階で得られたフタルイミド化合物2.20gに窒素雰囲気下、テトラヒドロフラン24ml、ヨードベンゼン2.11g、トリエチルアミン6.2mlを加え、還流下8時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.82gを得た。
段階C:1−メチル−4−フェニル−3−ブチニルアミン
上記段階で得られたフタルイミド体1.82gにメタノール63ml、ヒドラジン一水和物(80%)1.18gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム30mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミンを定量的に得た。
段階D:4−(1−メチル−4−フェニル−3−ブチニルアミノ)チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド20mlに上記段階で得られたアミン、4−クロロチエノ[2,3−d]ピリミジン1.02g、トリエチルアミン0.9mlを加え、80℃で4時間撹拌した。反応液に冷却後水30mlを加え、酢酸エチル50mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=9:1)で精製することによって目的生成物0.46gを得た。
同様の製造法により、表1、化合物No.230〜295,298,343〜354,381〜389を合成した。
ジクロロビス(トリフェニルホスフィン)パラジウム170mg、ヨウ化銅46mg、(2)で得られた4−[(3−ブチニル)アミノ]チエノ[2,3−d]ピリミジン0.97gに窒素雰囲気下、テトラヒドロフラン11m4−ヨード安息香酸メチル1.25g、トリエチルアミン2.9mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=1:1)で精製することによって、4−[4−(チエノ[2,3−d]ピリミジン−4−イルアミノ)−1−ブチニル]ベンゾエート1.09gを得た。
同様の製造法により、表1、化合物No.30,31,92,93,95,127,129を合成した。
段階A:4−ブロモ−2−フェニルチアゾール
テトラキス(トリフェニルホスフィン)パラジウム238mg、フェニルボロン酸0.55g、2,4−ジブロモチアゾール1.00gを入れたフラスコを窒素置換し、このフラスコにトルエン30ml、エタノール6.1ml、2Mの炭酸ナトリウム水溶液9.1mlを加え、還流下6時間撹拌した。室温まで冷却後、反応液に水50mlを加え酢酸エチル50mlで2回抽出した。有機層を飽和食塩水30mlで洗浄し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、ヘキサン:酢酸エチル=14:1)で精製することによって2−フェニル−4−ブロモチアゾール0.71gを得た。
段階B:2−[4−(2−フェニルチアゾール−4−イル)−3−ブチニル]イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム221mg、ヨウ化銅60mg、N−(3−ブチニル)フタルイミド1.24gに窒素雰囲気下、テトラヒドロフラン15ml、上記段階で得られた2−フェニル−4−ブロモチアゾール1.50g、トリエチルアミン3.8mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.24gを得た。
段階C:4−(2−フェニルチアゾール−4−イル)−3−ブチニルアミン
上記段階で得られたフタルイミド化合物1.24gにメタノール35ml、ヒドラジン一水和物(80%)0.65gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム20mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン0.96gを得た。
段階D:4−[4−(2−フェニルチアゾール−4−イル)−3−ブチニルアミノ]チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド13mlに上記段階で得られたアミン0.96g、4−クロロチエノ[2,3−d]ピリミジン0.68g、トリエチルアミン0.6mlを加え、85℃で4時間撹拌した。反応液に冷却後水25mlを加え、酢酸エチル30mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=2:1)で精製することによって目的生成物0.70gを得た。
同様の製造法により、表1、化合物No.77〜82を合成した。
段階A:2−ベンジル−4−ブロモチアゾール
テトラキス(トリフェニルホスフィン)パラジウム267mg、2,4−ジブロモチアゾール1.00gを入れたフラスコを窒素置換し、このフラスコに乾燥テトラヒドロフラン9ml、0.5Mの臭化ベンジル亜鉛テトラヒドロフラン溶液9.9mlを加え、70℃で6時間撹拌した。室温まで冷却後、反応液に水30mlを加え酢酸エチル30mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、ヘキサン:酢酸エチル=14:1)で精製することによって2−ベンジル−4−ブロモチアゾール0.36gを得た。
段階B:2−[4−(2−ベンジルチアゾール−4−イル)−3−ブチニル]イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム143mg、ヨウ化銅38mg、N−(3−ブチニル)フタルイミド0.80gに窒素雰囲気下、テトラヒドロフラン9ml、上記段階で得られた2−ベンジル−4−ブロモチアゾール1.02g、トリエチルアミン2.3mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.00gを得た。
段階C:4−(2−ベンジルチアゾール−4−イル)−3−ブチニルアミン
上記段階で得られたフタルイミド化合物1.00gにメタノール26ml、ヒドラジン一水和物(80%)0.50gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム25mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン0.12gを得た。
段階D:4−[4−(2−ベンジルチアゾール−4−イル)−3−ブチニルアミノ]チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド1.5mlに上記段階で得られたアミン0.12g、4−クロロチエノ[2,3−d]ピリミジン0.08g、トリエチルアミン0.1mlを加え、85℃で4時間撹拌した。反応液に冷却後水15mlを加え、酢酸エチル20mlで2回抽出した。有機層を水20mlで2回、さらに飽和食塩水20mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物0.07gを得た。
段階A:4−ブロモ−2−フェノキシチアゾール
N,N−ジメチルホルムアミド75mlに2,4−ジブロモチアゾール3.00g、フェノール1.74g、炭酸カリウム3.44gを加え、140℃で6時間撹拌した。室温まで冷却後、反応液に水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、飽和食塩水50mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、ヘキサン:酢酸エチル=9:1)で精製することによってエーテル化合物2.86gを得た。
段階B:2−[4−(2−フェノキシチアゾール−4−イル)−3−ブチニル]イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム399mg、ヨウ化銅109mg、N−(3−ブチニル)フタルイミド2.24gに窒素雰囲気下、テトラヒドロフラン26ml、上記段階で得られたエーテル化合物2.86g、トリエチルアミン6.9mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物3.50gを得た。
段階C:4−(2−フェノキシチアゾール−4−イル)−3−ブチニルアミン
上記段階で得られたフタルイミド化合物3.50gにメタノール90ml、ヒドラジン一水和物(80%)1.76gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム40mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン2.24gを得た。
段階D:4−[4−(2−フェノキシチアゾール−4−イル)−3−ブチニルアミノ]チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド27mlに上記段階で得られたアミン2.24g、4−クロロチエノ[2,3−d]ピリミジン1.45g、トリエチルアミン1.3mlを加え、85℃で4時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水50mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物2.79gを得た。
同様の製造法により、表1、化合物No.215〜228を合成した。
段階A:2−(4−チアゾリル−3−ブチニル)イソインドール−1,3−ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム1184mg、ヨウ化銅322mg、N−(3−ブチニル)フタルイミド6.64gに窒素雰囲気下、テトラヒドロフラン78ml、4−ブロモチアゾール5.49g、トリエチルアミン20.3mlを加え、還流下5時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって、フタルイミド化合物6.35gを得た。
段階B:4−チアゾリル−3−ブチニルアミン
上記段階で得られたフタルイミド化合物6.35gにエタノール115ml、水115ml、イオン交換樹脂(Diaion WA21J Resin)115mlを加え、90℃で2時間撹拌した。室温まで冷却後、イオン交換樹脂をろ過し、反応液を減圧下濃縮することによって、アミン2.48g得た。
段階C:4−[(4−チアゾリル−3−ブチニル)アミノ]チエノ[2,3−d]ピリミジン
N,N−ジメチルホルムアミド50mlに上記段階で得られたアミン2.48g、4−クロロチエノ[2,3−d]ピリミジン2.60g、トリエチルアミン2.3mlを加え、85℃で2.5時間撹拌した。反応液を冷却後、水を1L加え、析出した固体をろ過し、ろ物を水100mlで2回洗浄後、真空下乾燥する事で目的生成物3.00gを得た。
同様の製造法により、表1、化合物No.55〜60,62,63,68〜74,101,210を合成した。
段階A:1−フェニル−3−ブチニルアミン
テトラヒドロフラン4mlにベンズアルデヒド2.97gを加えた溶液に窒素雰囲気下、1Mのリチウムビストリメチルシリルアミドテトラヒドロフラン溶液を0℃で滴下した。この溶液を0℃で15分間、さらに室温で1時間撹拌した。この溶液を溶液Aとする。
亜鉛粉末6.03gに窒素雰囲気下、テトラヒドロフラン4ml、1,2−ジブロモエタン0.63gを加え、還流下1時間撹拌した。撹拌後、室温まで冷却後、クロロトリメチルシランのテトラヒドロフラン溶液(クロロトリメチルシラン0.37g+テトラヒドロフラン8ml)を室温で加えた。この溶液を−10℃に冷却し、プロパルギルブロミドのテトラヒドロフラン溶液(プロパルギルブロミド10.00g+テトラヒドロフラン8ml)を滴下し、さらに−10℃で1.5時間撹拌した。撹拌後、この溶液に溶液Aを−10℃で滴下し、適下後、徐々に室温まで上げ、室温で一晩撹拌した。反応液を0℃に冷却後、飽和炭酸カリウム溶液20mlを加え、さらに水65ml、メチルt−ブチルエーテル30mlを加えた。有機層を分液後、水層をさらにメチルt−ブチルエーテル30mlで5回抽出した。合わせた有機層を濃縮後、残渣を真空下乾燥した。この残渣に水を加え、メチルt−ブチルエーテル30mlで2回抽出し、有機層を水30mlで2回、飽和食塩水30mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、ろ液を濃縮し、真空下乾燥することでアミン3.38gを得た。
段階B:4−[(1−フェニル−3−ブチニル)アミノ]キナゾリン
N,N−ジメチルホルムアミド11mlに上記段階で得られたアミン0.49g、4−クロロキナゾリン0.50g、トリエチルアミン0.7mlを加え、85℃で3時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル20mlで2回抽出した。有機層を水20mlで2回、さらに飽和食塩水20mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物0.69gを得た。
ジクロロビス(トリフェニルホスフィン)パラジウム278mg、ヨウ化銅71mg、(11)で得られた4−[(1−フェニル−3−ブチニル)アミノ]キナゾリン2.00gに窒素雰囲気下、テトラヒドロフラン17m、ヨードベンゼン1.49g、トリエチルアミン4.5mlを加え、還流下3時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC−200、トルエン:酢酸エチル=4:1)で精製することによって、4−[(1,4−ジフェニル−3−ブチニル)アミノ]キナゾリン1.03gを得た。
同様の製造法により、表1、化合物No.302を合成した。
段階A:N−(ジフェニルメチレン)−2−(3−フェニル)プロパルギルグリシンエチル
窒素置換したフラスコにアセトニトリル50ml、N−(ジフェニルメチレン)グリシンエチル3.00g、3−フェニルプロパルギルブロマイド2.60g、炭酸カリウム2.32g、テトラブチルアンモニウム硫酸水素塩381mgを加え、24時間70度で撹拌した。室温に冷却後、この反応液に酢酸エチル100mlを加え、セライトろ過後、ろ液を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、N−(ジフェニルメチレン)−2−(3−フェニル)プロパルギルグリシンエチル2.00gを得た。
段階B:2−(3−フェニル)プロパルギルグリシンエチル
窒素置換したフラスコにジエチルエーテル20ml、上記段階で得られたアルコール1.80g、1N塩酸20mlを加え、そのまま室温で1日撹拌した。この反応液に重曹水30mlを加えたのち酢酸エチル50mlで2回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2−(3−フェニル)プロパルギルグリシンエチル985mgを得た。
段階C:4−[2−エトキシカルボニル−4−フェニル−3−ブチニルアミノ]キナゾリン
N,N−ジメチルホルムアミド15mlに上記段階で得られたアミン985mg、4−クロロキナゾリン720mg、トリエチルアミン1mlを加え、80℃で4時間撹拌した。反応液を冷却後、水40mlを加え、酢酸エチル70mlで2回抽出した。有機層を飽和食塩水40mlで2回洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、目的生成物1.10gを得た。
同様の製造法により、表1、化合物No.304を合成した。
テトラヒドロフラン10mlに4−[2−エトキシカルボニル−4−フェニル−3−ブチニルアミノ]キナゾリン200mg、リチウムジメチルアミノボロハイドライドの1Mテトラヒドロフラン溶液1mlを加え、室温で1時間撹拌した。反応液に1N塩酸20mlを加え、10分撹拌した。この反応液に重曹水を加え中和した後、酢酸エチル40mlで2回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、4−[2−ヒドロキシメチル−4−フェニル−3−ブチニルアミノ]キナゾリン37mgを得た。
テトラヒドロフラン5mlに4−[2−エトキシカルボニル−4−フェニル−3−ブチニルアミノ]キナゾリン130mg、40%メチルアミンメタノール溶液3mlを加え、60℃で1時間、室温で1昼夜撹拌した。反応液を濃縮後、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、4−[2−メチルアミノカルボニル−4−フェニル−3−ブチニルアミノ]キナゾリン113mgを得た。
段階A: 2−ビニル−4−フェニル−3−ブチンオール
窒素置換したフラスコに乾燥テトラヒドロフラン40ml、1.6Mのn−ブチルリチウム溶液20mlを−78℃で加え、30分撹拌した。この溶液にトリフルオロボランテトラヒドロフラン錯体3.5mlをゆっくりと滴下した。さらにこの溶液を15分、−78℃で撹拌し、1,3−ブタジエンモノエポキシド2.00gをゆっくり滴下し、さらに−78℃で3時間撹拌した。この反応液に飽和塩化アンモニウム水溶液50mlを加え、酢酸エチル100mlで1回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2−ビニル−4−フェニル−3−ブチンオール1.80gを得た。
段階B: 2−(2−ビニル−4−フェニル−3−ブチニル)イソインドール−1,3−ジオン
窒素置換したフラスコにトルエン55ml、2−ビニル−4−フェニル−3−ブチンオール1.80g、フタルイミド1.93g、トリフェニルホスフィン3.45gを加え、この溶液に氷冷下でジエチルアゾジカルボキシレート(40%トルエン溶液)5.30gをゆっくり滴下し、室温に昇温し1日撹拌した。反応液を濃縮後、残渣にジエチルエーテル200mlを加え、出てきた固体をろ別した。残渣を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2−(2−ビニル−4−フェニル−3−ブチニル)イソインドール−1,3−ジオン1.00gを得た。
段階C:2−ビニル−4−フェニル−3−ブチニルアミン
2−(2−ビニル−4−フェニル−3−ブチニル)イソインドール−1,3−ジオン1.00gにメタノール20ml、メチルアミン溶液(40%メタノール溶液)10mを加え、1時間60℃で撹拌した。反応液を濃縮し、酢酸エチル50ml、ジエチルエーテル50mlで順次洗浄後、ろ液を濃縮して粗生成物のアミン550mgを得た。
段階D:4−[2−ビニル−4−フェニル−3−ブチニルアミノ]キナゾリン
DMF15mlに2−ビニル−4−フェニル−3−ブチニルアミン550mg、4−クロロキナゾリン500mg、トリエチルアミン636μlを加え、80℃で5時間撹拌した。反応液を冷却後、水20mlを加え、酢酸エチル50mlで2回抽出した。有機層を飽和食塩水50mlで2回洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュ自動生成装置フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し目的生成物750mgを得た。
同様の製造法により、表1、化合物No.297を合成した。
製剤例1:乳剤
本発明化合物10部を、1,2−ジメチル−4−エチルベンゼン45部および1−メチル−2−ピロリジノン35部に溶解し、これにソルポール3005X(東邦化学工業株式会社製の界面活性剤の商品名)10部を加え、攪拌混合して10%乳剤を得た。
製剤例2:水和剤
本発明化合物10部を、ラウリル硫酸ナトリウム2部、リグニンスルホン酸ナトリウム4部、ホワイトカーボン20部およびクレー64部を混合した中に加え、ジュースミキサーで攪拌混合して10%水和剤を得た。
製剤例3:粒剤
本発明化合物5部に、ドデシルベンゼンスルホン酸ナトリウム2部、カルボキシメチルセルロース2部、ラウリル硫酸ナトリウム2部、ベントナイト10部およびクレー79部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して5%粒剤を得た。
製剤例4:粉剤
本発化合物1部を大豆油2部に溶解し、ホワイトカーボン5部、酸性リン酸イソプロピル(PAP)0.3部およびクレー91.7部を加え、ジュースミキサーで攪拌混合し、1%粉剤を得た。
製剤例5:フロアブル剤
本発明化合物20部とポリオキシエチレンアルキルエーテル、ジアルキルスルホサクシネートナトリウムおよび1,2−ベンズイソチアゾリン−3−オンをそれぞれ2部、1部および0.2部含む水20部を混合しダイノミルを用いて湿式粉砕後、プロピレングリコールおよびキサンタンガムをそれぞれ8部および0.32部含む水60部と混合し20%水中懸濁液を得た。
製剤例6:顆粒水和剤
本発明化合物20部に、ラウリル硫酸ナトリウム2部、アルキルナフタレンスルホン酸ナトリウム3部、デキストリン5部、ホワイトカーボン20部、クレー50部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して20%顆粒水和剤を得た。
(1)トマト疫病に対する防除効果試験
ポット植えトマト(品種;シュガーランプ、4.5葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にトマト疫病菌(Phytophthora infestans)の遊走子懸濁液(遊走子濃度1.0×104個/ml)を噴霧接種し、21℃の湿室条件下に1日置き、さらに温室に3日間置いて十分に発病させた後、各葉の発病程度を調査し、以下の式を用いて防除価を算出した。
防除価の算出;防除価={(無処理の発病面積率−処理した薬剤の発病面積率)/無処理の発病面積率}×100
算出された防除価を下記の基準に従って判定を行った。結果を表3に示す。
防除効果 高 : 100%≧防除価≧60%
防除効果 低 : 60%>防除価≧0%
ポット植えキュウリ(品種;相模半白、2.5葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にキュウリべと病菌(Pseudoperonospora cubensis)の分生子懸濁液(分生子濃度1.0×104個/ml)を噴霧接種した。接種後21℃の湿室条件下に1日置き、更に温室で3日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、試験例1と同様にして防除効果の判定を行った。結果を表4に示す。
ポット植えキュウリ(品種;相模半白、2葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にキュウリうどんこ病菌(Sphaerotheca fuliginea)の分生子懸濁液(分生子濃度1.0×105個/ml)を噴霧接種した。温室で14日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、試験例1と同様にして防除効果の判定を行った。結果を表5に示す。
直径3cmのキュウリ葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ワタアブラムシ(Aphis gossypii)雌成虫5頭を放飼し、一晩静置の後、産仔幼虫数を計数した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、二日後に死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表6に示す。
直径3cmのインゲン葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ナミハダニ(Tetranychus urticae)雌成虫10頭を放飼した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、二日後の死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表7に示す。
直径3cmのインゲン葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ナミハダニ(Tetranychus urticae)雌成虫10頭を放飼し、一晩室温条件下にて産卵させた後、放飼した雌成虫を除去した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、6日後の未孵化卵数を調査して殺卵率を算出した。殺卵率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表8に示す。
直径3cmのハクサイ葉片を、表1記載化合物の10%水和剤を500ppmに希釈調製した薬液に浸漬処理した後風乾させ、プラスチックシャーレに収容して、ハスモンヨトウ(Spodptera litura)3令幼虫10頭を放飼した。処理二日後の死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表9に示す。
表1記載化合物の10%水和剤を5000ppmに調製した希釈液を試験管に1mlとり、約200頭のサツマイモネコブセンチュウ(Meloidogyne incognita)を含む蒸留水9mlを添加して、48時間、室温に静置した。その後、薬液処理した線虫を洗い出し、顕微鏡下で生死を判別、殺線虫率を算出した。死亡率が95%以上をA、同80%以上95%未満をBと判定した。結果を表10に示す。
Claims (8)
- 次式[I]:
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0〜3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
b)炭素原子数1〜6個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニル、炭素原子数3〜8個のシクロアルキルまたは炭素原子数3〜8個のシクロアルケニル、
c)−SiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり全てが同じ置換基でも全てが異なる置換基でもよい)、
d)水素原子
から選択され、a)またはb)の場合、R1は−C(O)OR、−C(O)R、−R、−OR、−SR、−SO2R、−OC(O)R、−C(O)NHR、−C(O)NR2、−NHSO2R、−NRSO2R、−NHR、−NR2、−NHC(O)R、−NRC(O)R、−NHC(O)OR、−NRC(O)OR、−N(OR)C(O)OR、−NHSO2R、−NRSO2R、−SO2NHR、−SO2NR2(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、−SiR5R6R7、−OSiR5R6R7(R5,R6,R7は炭素原子数1〜6個の直鎖状又は分岐状のアルキル、フェニルであり2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、ハロアルキル、ハロアルケニル、ハロアルコキシ、アシルアルコキシ、アシルオキシアルキル、アルキルスルホニルアルキル、シロキシアルキル、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、アルキルチオアルキル、ジアルコキシアセタール、アルコキシアルコキシ、シアノアルキル、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾジオキソリル、イミド、ホルミル(−CHO)、カルボキシル(−COOH)、ホルムアミド(−NHCHO)、環状エーテル、および環状アミンで置換されていてもよく、
R2は水素原子、−R、−OR、−C(O)OR、−C(O)NHR、−CONR2(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、フェニル、ヘテロアリール、ハロゲン、シアノ、ハロアルキル、ハロアルコキシを表し、
R3は(1)水素原子、(2)ハロゲン原子、(3)(炭素原子数1〜8個の直鎖状又は分岐状の脂肪族炭化水素基)−CO−O−で表されるアシルオキシ、、ハロゲン原子若しくは水酸基で置換された炭素原子数1〜6個のアルキル、(4)無置換の炭素原子数1〜6個のアルキル、(5)−OR、−SR、−SO2R(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、または(6)ハロアルキルを表し、
R4は水素原子、ハロゲン原子、炭素原子数1〜6個のアルキル、ニトロ、アミノ、フェニル、ベンジル又はR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表す。]
で示される4−(3−ブチニル)アミノピリミジン誘導体。 - R4がR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環である、請求項1に記載の化合物。
- R4がR3と結合してピリミジン環上の炭素原子と共に形成するベンゼン環である、請求項1に記載の化合物。
- R3が1ないしは複数個のハロゲン原子で置換された炭素原子数1〜6個のアルキル、R4がハロゲン原子である、請求項1に記載の化合物。
- R2が水素原子、ハロゲン原子、シアノ基、フェニル、ヘテロアリール、−R、−C(O)OR、−C(O)NHR(ここでのRは、炭素原子数1〜8個の直鎖状又は分岐状のアルキル、炭素原子数2〜8個の直鎖状又は分岐状のアルケニル、炭素原子数2〜8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3〜8個のシクロアルキルである)、ヒドロキシアルキル、アルコキシアルキルである、請求項1に記載の化合物。
- R1がフェニル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、ピリジル、ベンゾチアゾリル、ピロリル、ベンゾオキサゾリル、ピラジニル、チエニル、イミダゾリルから成る群より選択される、0〜3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環から選択される、請求項1に記載の化合物。
- 請求項1に記載の式[I]で示される4−(3−ブチニル)アミノピリミジン誘導体を有効成分として1種若しくは2種以上含む有害生物防除剤。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011522855A JP5325297B2 (ja) | 2009-07-16 | 2010-07-15 | 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009168286 | 2009-07-16 | ||
JP2009168286 | 2009-07-16 | ||
JP2010101951 | 2010-04-27 | ||
JP2010101951 | 2010-04-27 | ||
PCT/JP2010/061993 WO2011007839A1 (ja) | 2009-07-16 | 2010-07-15 | 農園芸用の有害生物防除剤としての4-(3-ブチニル)アミノピリミジン誘導体 |
JP2011522855A JP5325297B2 (ja) | 2009-07-16 | 2010-07-15 | 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2011007839A1 JPWO2011007839A1 (ja) | 2012-12-27 |
JP5325297B2 true JP5325297B2 (ja) | 2013-10-23 |
Family
ID=43449448
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011522855A Expired - Fee Related JP5325297B2 (ja) | 2009-07-16 | 2010-07-15 | 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 |
Country Status (12)
Country | Link |
---|---|
US (1) | US8586505B2 (ja) |
EP (1) | EP2455371B1 (ja) |
JP (1) | JP5325297B2 (ja) |
AU (1) | AU2010271805B2 (ja) |
CA (1) | CA2765661C (ja) |
ES (1) | ES2443154T3 (ja) |
IL (1) | IL217078A (ja) |
NZ (1) | NZ597198A (ja) |
PL (1) | PL2455371T3 (ja) |
PT (1) | PT2455371E (ja) |
TW (1) | TWI485138B (ja) |
WO (1) | WO2011007839A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012148981A (ja) * | 2011-01-14 | 2012-08-09 | Sds Biotech Corp | 農園芸用の有害生物防除剤としてのピリミジン誘導体 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2012096115A1 (ja) * | 2011-01-14 | 2014-06-09 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としての含フッ素キナゾリン誘導体 |
WO2012096129A1 (ja) * | 2011-01-14 | 2012-07-19 | 株式会社エス・ディー・エス バイオテック | 4-(3-ブチニル)アミノピリミジン誘導体を含む農園芸用有害生物防除剤組成物 |
WO2012096137A1 (ja) * | 2011-01-14 | 2012-07-19 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としてのキナゾリン誘導体 |
AR088218A1 (es) | 2011-07-19 | 2014-05-21 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos utiles como inhibidores de pi3k |
JP2015512891A (ja) | 2012-03-13 | 2015-04-30 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 殺菌性ピリミジン化合物 |
SG11201406858WA (en) * | 2012-04-24 | 2014-11-27 | Stepan Co | Unsaturated fatty alcohol derivatives from natural oil metathesis |
EP2835052A1 (en) * | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
WO2015036058A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
CN103577187A (zh) * | 2013-10-15 | 2014-02-12 | 中兴通讯股份有限公司 | 一种实现网页截图的方法及相关设备 |
MX2018012687A (es) * | 2016-05-12 | 2019-01-31 | Res Triangle Inst | Fenitelaminas vinílogas como liberadores de neurotransmisores. |
WO2022212531A1 (en) * | 2021-03-31 | 2022-10-06 | Acerand Therapeutics (Usa) Limited | Pyridopyrimidinone compounds |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004087706A1 (de) * | 2003-04-02 | 2004-10-14 | Basf Aktiengesellschaft | 7-alkinylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
WO2006047397A1 (en) * | 2004-10-21 | 2006-05-04 | Dow Agrosciences Llc | Thieno-pyrimidine compounds having fungicidal activity |
WO2007046809A1 (en) * | 2005-10-21 | 2007-04-26 | Dow Agrosciences Llc | Thieno-pyrimidine compounds having fungicidal activity |
WO2007135029A1 (en) * | 2006-05-22 | 2007-11-29 | Basf Se | Insecticidal methods using 4-amino-5-chloro-thieno[2,3-d]-pyrimidine compounds |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1570494A (en) * | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
EP0519211A1 (de) * | 1991-05-17 | 1992-12-23 | Hoechst Schering AgrEvo GmbH | Substituierte 4-Aminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
JP2673848B2 (ja) | 1992-02-18 | 1997-11-05 | 宇部興産株式会社 | アルキルアミノピリミジン誘導体、その製法及び有害生物防除剤 |
JP2649125B2 (ja) | 1992-07-10 | 1997-09-03 | 宇部興産株式会社 | アルキルアミノピリミジン誘導体、その製法及び有害生物防除剤 |
DE4331180A1 (de) * | 1993-09-14 | 1995-03-16 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
JP3211636B2 (ja) | 1994-08-23 | 2001-09-25 | 宇部興産株式会社 | 4−シクロヘキシルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤 |
JPH11158161A (ja) | 1997-11-28 | 1999-06-15 | Ube Ind Ltd | 4−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤 |
JP3903585B2 (ja) | 1998-04-17 | 2007-04-11 | 宇部興産株式会社 | 5−ヨード−4−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤 |
US6521627B1 (en) | 1998-04-14 | 2003-02-18 | Ube Industries, Ltd. | 5-Iodo-4-phenethylaminopyrimidine derivative, intermediate thereof, processes for producing the same and agricultural and horticultural pesticides |
JP4186484B2 (ja) * | 2002-03-12 | 2008-11-26 | 住友化学株式会社 | ピリミジン化合物およびその用途 |
JP2006008542A (ja) | 2004-06-23 | 2006-01-12 | Ube Ind Ltd | 4−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤 |
WO2007083692A1 (ja) * | 2006-01-23 | 2007-07-26 | Kumiai Chemical Industry Co., Ltd. | アミノピリミジン誘導体及び農園芸用植物病害防除剤 |
-
2010
- 2010-07-15 WO PCT/JP2010/061993 patent/WO2011007839A1/ja active Application Filing
- 2010-07-15 PT PT107998973T patent/PT2455371E/pt unknown
- 2010-07-15 CA CA2765661A patent/CA2765661C/en not_active Expired - Fee Related
- 2010-07-15 JP JP2011522855A patent/JP5325297B2/ja not_active Expired - Fee Related
- 2010-07-15 US US13/378,866 patent/US8586505B2/en not_active Expired - Fee Related
- 2010-07-15 ES ES10799897.3T patent/ES2443154T3/es active Active
- 2010-07-15 TW TW099123402A patent/TWI485138B/zh not_active IP Right Cessation
- 2010-07-15 NZ NZ597198A patent/NZ597198A/xx unknown
- 2010-07-15 PL PL10799897T patent/PL2455371T3/pl unknown
- 2010-07-15 AU AU2010271805A patent/AU2010271805B2/en not_active Ceased
- 2010-07-15 EP EP10799897.3A patent/EP2455371B1/en not_active Not-in-force
-
2011
- 2011-12-19 IL IL217078A patent/IL217078A/en not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004087706A1 (de) * | 2003-04-02 | 2004-10-14 | Basf Aktiengesellschaft | 7-alkinylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
WO2006047397A1 (en) * | 2004-10-21 | 2006-05-04 | Dow Agrosciences Llc | Thieno-pyrimidine compounds having fungicidal activity |
WO2007046809A1 (en) * | 2005-10-21 | 2007-04-26 | Dow Agrosciences Llc | Thieno-pyrimidine compounds having fungicidal activity |
WO2007135029A1 (en) * | 2006-05-22 | 2007-11-29 | Basf Se | Insecticidal methods using 4-amino-5-chloro-thieno[2,3-d]-pyrimidine compounds |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012148981A (ja) * | 2011-01-14 | 2012-08-09 | Sds Biotech Corp | 農園芸用の有害生物防除剤としてのピリミジン誘導体 |
Also Published As
Publication number | Publication date |
---|---|
AU2010271805B2 (en) | 2014-11-13 |
PT2455371E (pt) | 2014-01-20 |
JPWO2011007839A1 (ja) | 2012-12-27 |
EP2455371B1 (en) | 2013-12-25 |
US8586505B2 (en) | 2013-11-19 |
TWI485138B (zh) | 2015-05-21 |
NZ597198A (en) | 2013-05-31 |
CA2765661A1 (en) | 2011-01-20 |
PL2455371T3 (pl) | 2014-05-30 |
EP2455371A4 (en) | 2013-01-23 |
ES2443154T3 (es) | 2014-02-18 |
WO2011007839A1 (ja) | 2011-01-20 |
EP2455371A1 (en) | 2012-05-23 |
TW201114748A (en) | 2011-05-01 |
CA2765661C (en) | 2016-12-20 |
IL217078A (en) | 2015-05-31 |
AU2010271805A1 (en) | 2012-01-19 |
US20120136150A1 (en) | 2012-05-31 |
IL217078A0 (en) | 2012-02-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5325297B2 (ja) | 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 | |
JP5902100B2 (ja) | 4−(3−ブチニル)アミノピリミジン誘導体を含む農園芸用有害生物防除剤組成物 | |
CN104185628B (zh) | 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途 | |
CN111741951B (zh) | 酰胺化合物或其盐类、以及含有这些化合物的农业园艺用杀菌剂及其使用方法 | |
JPWO2012096137A1 (ja) | 農園芸用の有害生物防除剤としてのキナゾリン誘導体 | |
JPWO2012096115A1 (ja) | 農園芸用の有害生物防除剤としての含フッ素キナゾリン誘導体 | |
JPWO2014065411A1 (ja) | 農園芸用の有害生物防除剤としてのスルホンアミド誘導体 | |
JP5731205B2 (ja) | 農園芸用の有害生物防除剤としてのピリミジン誘導体 | |
CN114008045B (zh) | 以新的咪唑并吡啶-2-羧酰胺衍生物为有效成分的农业园艺用药剂 | |
JP5425909B2 (ja) | 新規な4−複素環置換ピリミジン誘導体、及びそれらを含有する農園芸用有害生物防除剤 | |
JP2004035499A (ja) | フェニルカーバメート化合物および農園芸用殺菌殺虫剤 | |
JP2005126418A (ja) | 置換ベンズアニリド化合物及び有害生物防除剤 | |
WO2024117205A1 (ja) | 双環式ピリジン誘導体およびその塩、並びに、当該誘導体又はその塩を有効成分として含有することを特徴とする有害生物防除剤 | |
JP2005008630A (ja) | シクロアルキル置換ベンズアニリド化合物及び有害生物防除剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130620 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130719 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5325297 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |