CN1133046A - 用作农药的硫代磷酸酯 - Google Patents
用作农药的硫代磷酸酯 Download PDFInfo
- Publication number
- CN1133046A CN1133046A CN 94193706 CN94193706A CN1133046A CN 1133046 A CN1133046 A CN 1133046A CN 94193706 CN94193706 CN 94193706 CN 94193706 A CN94193706 A CN 94193706A CN 1133046 A CN1133046 A CN 1133046A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- optional
- representative
- halogen
- alkoxyl group
- 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.)
- Pending
Links
- 239000000575 pesticide Substances 0.000 title abstract description 4
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 40
- 239000000460 chlorine Substances 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 32
- 229910052731 fluorine Inorganic materials 0.000 description 32
- 239000011737 fluorine Substances 0.000 description 32
- 230000000694 effects Effects 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 239000003995 emulsifying agent Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- -1 benzene thiocarbonyl group phosphonic acid ester Chemical class 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical group ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 230000001066 destructive effect Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 5
- 235000011330 Armoracia rusticana Nutrition 0.000 description 5
- 240000003291 Armoracia rusticana Species 0.000 description 5
- 241000086608 Empoasca vitis Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000272639 Brachycaudus mimeuri Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000578422 Graphosoma lineatum Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical group CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 3
- 235000011303 Brassica alboglabra Nutrition 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 235000011302 Brassica oleracea Nutrition 0.000 description 3
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 3
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 3
- 241000675108 Citrus tangerina Species 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 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 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 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
- 239000007787 solid Substances 0.000 description 3
- 239000012747 synergistic agent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001427559 Collembola Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000738498 Epitrix pubescens Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001649229 Psoroptes Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000130771 Tinea pellionella Species 0.000 description 2
- 241000255901 Tortricidae Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JCXVPCYMKJTPEE-UHFFFAOYSA-N methyl n-hydroxyethanimidate Chemical compound COC(C)=NO JCXVPCYMKJTPEE-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- PBQZQTQFQFYBNJ-UHFFFAOYSA-N n-methoxybenzamide Chemical compound CONC(=O)C1=CC=CC=C1 PBQZQTQFQFYBNJ-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000934064 Acarus siro Species 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000059559 Agriotes sordidus Species 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001427556 Anoplura Species 0.000 description 1
- 241001435074 Anthomyia Species 0.000 description 1
- 241000254177 Anthonomus Species 0.000 description 1
- 241001414828 Aonidiella aurantii Species 0.000 description 1
- 241000134843 Aphelenchoides besseyi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241001480748 Argas Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001142394 Bibio marci Species 0.000 description 1
- 241000238659 Blatta Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000238678 Boophilus Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 244000308180 Brassica oleracea var. italica Species 0.000 description 1
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- 241000982105 Brevicoryne brassicae Species 0.000 description 1
- 241000398201 Bryobia praetiosa Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000259759 Cassida nobilis Species 0.000 description 1
- 241001674939 Caulanthus Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241000040710 Chela Species 0.000 description 1
- 241000931705 Cicada Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241001498622 Cixius wagneri Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000592374 Daktulosphaira vitifoliae Species 0.000 description 1
- 241000268912 Damalinia Species 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000399949 Ditylenchus dipsaci Species 0.000 description 1
- 108700004685 Drosophila y Proteins 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000223924 Eimeria Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000283070 Equus zebra Species 0.000 description 1
- 241000917107 Eriosoma lanigerum Species 0.000 description 1
- 241000917171 Eriosomatinae Species 0.000 description 1
- 241001331999 Euproctis Species 0.000 description 1
- 241000371383 Fannia Species 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- 241000241125 Gryllotalpa gryllotalpa Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001659689 Hercinothrips Species 0.000 description 1
- 241001466007 Heteroptera Species 0.000 description 1
- 241000771999 Hippobosca Species 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 241001480803 Hyalomma Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241000832180 Hylotrupes bajulus Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241001495069 Ischnocera Species 0.000 description 1
- 241001149911 Isopoda Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241000270322 Lepidosauria Species 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 240000000233 Melia azedarach Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000406465 Neodiprion Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 241001585712 Noctua Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000168255 Opiliones Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241000532856 Otiorhynchus sulcatus Species 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 241001675061 Phaedon brassicae Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 241001401863 Phorodon Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000013992 Prunus padus Nutrition 0.000 description 1
- 244000078856 Prunus padus Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241001105129 Ptinus Species 0.000 description 1
- 241000201375 Radopholus similis Species 0.000 description 1
- 241001509970 Reticulitermes <genus> Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000253973 Schistocerca gregaria Species 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000180219 Sitobion avenae Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001481659 Syrphidae Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001124685 Tenthredinidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241001259047 Trichodectes Species 0.000 description 1
- 241001220308 Trichodorus Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000201423 Xiphinema Species 0.000 description 1
- 241001466330 Yponomeuta malinellus Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 230000006837 decompression Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及通式(I)的新的硫代磷酸酯。其中,R代表任选取代的烷基;R1代表任选取代的烷基;R2代表任选取代的烷基;和R3代表任选取代的烷基、任选取代的环烷基或任选取代的芳基;它们可用作农药。
Description
本发明涉及新的取代的硫代磷酸酯,它们的制备方法以及它们作为农药的应用,特别是用作杀虫剂、杀螨剂和杀线虫剂的应用。
已公开的是,某些取代的苯硫羰基膦酸酯和亚氨苄基硫羰基硫代磷酸酯具有杀虫、杀螨和杀线虫性质(参看EP-A0116254和DE-A-2545392)。但这些已知化合物的活性在某些情况下,特别是当使用量低和浓度低时,活性化合物并不总是完全令人满意。
已经发现通式(I)的新的取代的硫代磷酸酯其中,R代表任选取代的烷基;
R1代表任选取代的烷基;
R2代表任选取代的烷基;和
R3代表任选取代的烷基、任选取代的环烷基或任选取代的芳
基。
此外,还已发现通式(I)的新的取代的硫代磷酸酯可以下述方式得到:a)适宜时,在酸受体存在下,并且适宜时,在稀释剂存在下,使通式(II)的氯代硫代磷酸酯与通式(Ⅲ)的化合物反应,其中,R和R1具有上述含义;其中,R2和R3具有上述含义,或b)在第一反应步骤中,适宜时在酸受体存在下,并且适宜时在稀释剂存在下,使通式(IV)的硫代磷酰二氯与通式(V)的醇反应,其中,R1具有前述意义;
R-OH (V)其中,R具有前述意义;和
通式(I)的新化合物具有足以使它们用作农药的性质。它们对节肢动物和线虫具有很强的作用,并特别可用于防治昆虫、螨和线虫。
上述和下述的式中提及的优选取代基或取代基的范围说明于下:
在通式中,烷基指优选含1至8个碳原子,特别是1至6个碳原子,尤其优选1至5个碳原子,更尤其优选1至4个碳原子的直链或支链烷基。下列基团可提及作为优选烷基:甲基、乙基、正丙基和异丙基、正、异、仲和叔-丁基、戊基、己基和辛基。
在通式中,环烷基优选指优选含3至7,特别是3至6,特别优选5或6个环碳原子的单环环烷基,优选环戊基和环己基,特别是环己基。
在通式中,芳基优选指含6至10个碳原子的芳基(优选苯基或萘基),特别优选苯基。
烷基R、R1和R2可被相同或不相同的取代基单取代或多取代(优选单取代至5取代,特别是单取代至3取代),可提及的优选取代基是卤素(优选氟、氯、溴和/或碘,特别是氟和/或氯)和/或含优选1至4,特别是1或2个碳原子的烷氧基。烷基R、R1和R2以及环烷基R3特别优选是未取代的。
提及的用作R3的烷基、环烷基和芳基可被1个或多个,优选1至5个,特别是1至3个并且特别优选1或2个相同或不相同的取代基取代,优选的取代基为:卤素,优选氟、氯、溴和/或碘,特别优选氟和/或氯,尤其特别优选氯;含1至4个碳原子,特别优选1或2个碳原子的烷氧基,尤其特别优选甲氧基;含优选1至4个,尤其优选1或2个碳原子以及优选1至5,优选1至3个相同或不相同卤原子(优选氟、氯和/或溴,特别优选氟和/或氯,尤其特别优选氯)的卤代烷氧基。环烷基和芳基可进一步(并且适宜时,再)被1个或多个,优选1至3个,特别是1个或2个下列基团取代:含优选1至4个,特别是1至3个,特别优选1或2个碳原子的烷基,烷基还可含1个或多个,优选1至5个,特别是1至3个相同或不相同的卤原子(优选氟、氯、溴和/或碘,特别是氟和/或氯,特别优选氯);硝基和/或氰基(CN)。苯基R3特别优选被卤素(优选氯)取代或未取代。在通式中
R优选代表任选被卤素(优选氟和/或氯)和/或C1-C4
烷氧基取代的C1-C6烷基;在通式中
R1优选代表任选被卤素(优选氟和/或氯)和/或C1-C4
烷氧基取代的C1-C6烷基;在通式中
R2优选代表任选被卤素(优选氟和/或氯)和/或C1-C4
烷氧基取代的C1-C6烷基;在通式中
R3优选代表任选被卤素(优选氟和/或氯)和/或C1-C4
烷氧基取代的C1-C6烷基、任选被卤素(优选氟和/或
氯)和/或C1-C4烷基和/或C1-C4烷氧基取代的
C3-C7环烷基,其中C1-C4烷基和C1-C4烷氧
基可被卤素(优选氟和/或氯)取代,或者代表可含一个或
多个相同或不相同的选自下列基团的取代基的苯基:
卤素(优选氟和/或氯)、C1-C4烷基和/或C1-C4
烷氧基,其中C1-C4烷基和C1-C4烷氧基可被卤素
(优选氟和/或氯)取代、硝基和/或氰基(CN)。在通式中
R特别优选代表任选被卤素(优选氟和/或氯)和/或C1-
C4烷氧基取代的C1-C4烷基;在通式中
R1特别优选代表任选被卤素(优选氟和/或氯)和/或C1-
C4烷氧基取代的C1-C4烷基;在通式中
R2特别优选代表任选被卤素(优选氟和/或氯)和/或C1-
C4烷氧基取代的C1-C4烷基;在通式中
R3特别优选代表任选被卤素(优选氟和/或氯)和/或C1-C4
烷氧基取代的C1-C5烷基、或代表任选被卤素(优选氟
和/或氯)和/或C1-C4烷基和/或C1-C4烷氧基
取代的C3-C5环烷基,其中C1-C4烷基和C1-C4
烷氧基可被卤素(优选氟和/或氯)取代,或代表可含一个
或多个相同或不相同的选自下列基团的取代基的苯基:
卤素(优选氟和/或氯)、C1-C4烷基和/或C1-C4
烷氧基,其中C1-C4烷基和C1-C4烷氧基可被卤素
(优选氟和/或氯)取代、硝基和/或氰基(CN)。在通式中
R尤其特别优选代表任选被卤素(优选氟和/或氯)和/或
C1-C2烷氧基取代的C1-C4烷基;在通式中
R1尤其特别优选代表任选被卤素(优选氟和/或氯)和/或
C1-C2烷氧基取代的C1-C4烷基;在通式中
R2尤其特别优选代表任选被卤素(优选氟和/或氯)和/或
C1-C2烷氧基取代的C1-C4烷基;在通式中
R3尤其特别优选代表任选被卤素(优选氟和/或氯)和/或
C1-C2烷氧基取代的C1-C5烷基;或代表任被卤素
(优选氟和/或氯)和/或C1-C2烷基和/或C1-C2
烷氧基取代的C3-C6环烷基,其中C1-C2烷基和
C1-C2烷氧基可被卤素(优选氟和/或氯)取代;或代
表可含有1个或多个相同或不同的选自下列基团的取代基的
苯基:
卤素(优选氟和/或氯);C1-C2烷基和/或C1-C2
烷氧基,其中C1-C2烷基和C1-C2烷氧基可被卤素
(优选氟和/或氯)取代;硝基和/或氰基(CN)。在通式中,
R极为特别代表C1-C4烷基。在通式中
R1极为特别代表C1-C4烷基。在通式中
R2极为特别代表C1-G4烷基。在通式中
R3极为特别代表C1-C5烷基,它任选被氯和/或C1-C2
烷氧基取代;或代表任选被氯取代的苯基或C3-C6环烷
基。在通式中
R尤其极为特别代表甲基、乙基或正丙基,特别是乙基或正丙
基。在通式中
R1尤其极为特别代表正丙基、异丙基或仲丁基,特别是仲丁基。在通式中
R2尤其极为特别代表甲基、乙基和异丙基及正丙基,特别是甲
基。在通式中
R3尤其极为特别代表甲基、乙基、正丙基、异丙基、仲丁基、
叔丁基、1-乙基丙基、甲氧基甲基、环己基、苯基或氯苯
基。
无论是一般情况下还是在给出优选范围的情况下,各基团的上述定义或说明都可以按需要互相组合,也就是说可以组合各自的范围和优选范围。这适用于最终产物,也同样适用于起始物和中间体。
本发明的优选的通式(I)化合物为其中组合了上述优选定义的那些化合物。
本发明特别优选的通式(I)化合物为其中组合了上述特别优选定义的那些化合物。
本发明尤其特别优选的通式(I)化合物为其中组合了上述尤其特别优选定义的那些化合物。
本发明的极为特别的通式(I)的化合物为其中组合了极为特别的定义的那些化合物。
本发明的尤其极为特别的通式(I)化合物为其中组合了尤其极为特别的定义的那些化合物。
例如,经S-丙基二氯代硫代磷酸酯、乙醇和O-甲基苯氧肟酸作起始物时,本发明方法(b)的反应过程可用下列方程式表示:
通式II、Ⅲ、Ⅳ和V的起始物为已知或可用已知方法和工艺制得。
本发明制备新的通式(I)的化合物的方法优选采用稀释剂进行实施。适用的稀释剂几乎为所有惰性有机溶剂。这些优选包括脂族和芳族并且优选卤代的烃类,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯化碳、氯苯和邻二氯苯,醚类,例如乙醚和丁醚、乙二醇二甲醚和二甘醇二甲醚、四氢呋喃和二噁烷,酮类,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮,酯类,例如乙酸甲酯和乙酸乙酯,腈类,例如乙腈和丙腈,酰胺类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,以及二甲基亚砜、四亚甲基砜和六甲基磷酰三胺。
可用于实施本发明方法的酸受体为所有可常规用于这类反应的酸结合试剂。下列为优选适合的试剂:碱金属氢化物和碱土金属氢化物,例如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氢氧化物和碱土金属氢氧化物,例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属碳酸盐,碱金属碳酸氢盐、碱土金属碳酸盐和碱土金属碳酸氢盐,例如碳酸钠、碳酸氢钠、碳酸钾和碳酸氢钾以及碳酸钙,碱金属乙酸盐,例如乙酸钠和乙酸钾、碱金属醇盐,例如叔丁醇钠和叔丁醇钾,以及碱性氮化物,例如三甲胺、三乙胺、三丙胺、三丁胺、二异丁胺、二环己胺、乙基二异丙基胺、乙基二环己基胺、N,N-二甲基苄胺、N,N-二甲基苯胺、吡啶、2-甲基、3-甲基、4-甲基、2,4-二甲基、2,6-二甲基、2-乙基、4-乙基和5-乙基-2-甲基-吡啶、1,5-二氮杂双环[4.3.0]壬-5-烯(DNB)、1,8-二氮杂双环[5.4.0]-十一-7-烯(DBU)和1,4-二氮杂双环[2.2.2]-辛烷(DABCO)。
本发明方法中的反应温度可在宽范围内变化。一般而言,所述方法在0-100℃温度,优选在10-80℃温度实施。
本发明方法一般在大气压下实施,但也可能在高压或减压下实施所述方法。
实施本发明方法时,多种情况下所需的起始物优选以近似等摩尔量使用。但也可能以大过量使用各种情况下所用各组分中的一种组分。反应在适宜溶剂中在酸受体存在下进行,并且反应混合物在各自所需的反应温度下搅拌数小时。本发明方法的后处理分别用常规方法进行(参见制备实施例)。
在方法(b)中,通式(II)的化合物优选不分离。
在大多数情况下,新化合物以油状物形式得到,其中某些化合物不可能在不分解的条件下进行蒸馏,但通过所谓的“早期蒸馏(incipient distillation)”,也即在减压下延长加热到中等高温的过程而脱除最后的挥发性组分,并由此进行纯化。它们以折光指数进行表征。
活性化合物适用于防治害虫,特别是在农业、林业以及储存产品和材料的保护以及卫生部门中出现的昆虫、蜘蛛纲动物以及线虫,并且有好的植物耐受性,在对温血动物的毒性方面也较有利。它们对于通常敏感和有抗性的物种及其全部或部分发育阶段具有活性。上述害虫包括:
等足目,例如潮虫、平甲虫和鼠妇。
倍足目,例如具斑马陆。
唇足目,例如食果地蜈蚣和蛐蜒属。
扁肩象目,例如庭院么蛐。
缨尾目,例如西洋衣鱼。
弹尾目,例如具刺跳虫。
直翅目,例如东方蜚蠊、美国大蠊、马得拉蜚蠊、德国蠊、家蟋蟀、蝼姑属、热带飞蝗、殊种蚱蜢和沙漠蝗。
革翅目,例如欧洲球螋。
等翅目,例如犀白蚁属。
虱目,例如葡萄瘤蚜、绵蚜属、体虱、血虱属和长颚虱属。
食毛目,例如嚼虱属和畜虱属。
缨翅目,例如温室条蓟马和葱蓟马。
异翅亚目,例如扁盾蝽属、红蝽属、方背皮蝽属、温带臭虫、长红蜡蝽和蜡蝽属。
半翅目,例如甘监粉虱、木薯粉虱、温室粉虱、棉蚜、甘蓝蚜、茶蔗隐瘤蚜、Doralis fabae、Doralis Pomi、苹果绵蚜、桃大尾蚜、稠李溢管蚜、微叶蝉属、双叶叶蝉、黑尾叶蝉、麦长管蚜、瘤蚜属、忽布疣蚜、李蜡蚧、油榄黑盔蚧、灰飞虱、稻褐飞虱、红圆蚧、夹竹桃圆蚧、粉蚧属和木虱属。
鳞刺目,例如棉红蛉虫、松天蚜、冬天蛾、苹细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾、桔叶潜蛾、地虎属、刀根虫属、夜蛾属、棉斑实蛾、实夜蛾属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、粘虫属、粉纹夜蛾、苹蠢蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织衣蛾、亚麻黄卷蛾、具网卷叶蛾、云松卷蛾、葡萄果蠢蛾、茶长卷蛾和栎绿卷叶蛾。
鞘翅目,例如具斑窃蠢、谷蠢、豆象、大豆象、家天牛、赤杨紫跳甲、马铃薯甲虫、辣根猿叶虫、叶甲属、油菜蓝跳甲、墨西哥豆飘虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑象甲、香蕉根象甲、甘蓝荚象甲、苜蓿叶象甲、皮蠢属、斑皮蠢属、圆皮蠢属、毛皮蠢属、粉蠢属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、大黄粉虫、叩甲属、金针虫属、西方五月鳃角金龟、六月金龟和褐新西兰肋翅角金龟。
膜刺目,例如锯角叶蜂属、叶蜂属、蚁尾属、厕蚁和胡蜂属。
双翅目,如伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、厩螯蝇属、狂蝇属、皮蝇属、虻属、螗蜩属、花圆毛蚊、瑞典麦杆蝇、麦花蝇属、菠菜潜叶花蝇、地中海实蝇、油榄实蝇和欧洲大蚊。
蚤目,如印度客蚤和毛列蚤属。
蛛形纲,如蝎和盗蛛。
蜱螨目,如粗脚粉螨、锐缘蜱属、纯缘蜱属、鸡皮刺螨、茶蔗瘿螨、桔芸锈螨、牛蜱属、扁头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿苔螨、全爪螨属和叶螨属。
植物寄生线虫包括根线虫类、Radopholus Similis、玉米茎线虫、桔根线虫、根结线虫类、Meloidogyne Spp、稻干尖线虫、LongidorusSpp、Xiphinema Spp、Trichodorus Spp。
活性化合物可调制成常规的制剂,如溶液剂、乳液剂、粉末剂、泡沫剂、尘剂、糊剂、颗粒剂、气胶剂、浸泡了活性化合物的天然和合成材料,用于种子的在高分子物质和涂层组合物中的微胶囊剂。以及和燃烧设备(如熏蒸筒、熏蒸罐和熏蒸盘管等)一起使用的制剂,以及ULV冷雾和热雾剂。
这些制剂用已知方法制成,例如可通过下述方法:任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物和稀释剂(即液体溶剂、高压下液化的气体和/或固体载体)混合。如果采用水作稀释剂,则也可用(例如)有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘)、氯化芳族化合物和氯代脂族烃类(如氯苯、二氯乙烷或二氯甲烷)、脂族烃类(如环己烷或烷属烃,如矿物油馏分)、醇类(如丁醇或乙二醇及它们的醚或酯)、酮类(如丙酮、甲基乙基酮、甲基异丁基酮或环己酮)、强极性溶剂(如二甲基甲酰胺和二甲基亚砜以及水);液化的气体稀释剂或载体指在环境温度和大气压下为气体的液体,如气溶胶推进剂,如卤代烃类以及丁烷、丙烷、氮气和二氧化碳;适用的固体载体有:如研碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱土或硅藻土)和研碎的合成矿物(如高分散度硅石、氧化铝和硅酸盐);适用的固体颗粒载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及合成的无机颗粒和有机粉,和有机材料颗粒(如锯末、椰壳、玉米棒碎块和烟叶杆);适用的乳化剂和/或起泡剂有:如非离子型和阴离子型乳化剂(如聚氧乙烯脂肪酸酸、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐及蛋清水解产物);适用的分散剂有:如亚硫酸纸浆废液、甲基纤维素。
在制剂中可使用粘合剂,例如羧甲基纤维素和粉状、颗粒状或胶乳状天然和合成高聚物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯以及天然磷脂,如脑磷脂和卵磷脂以及合成磷脂。其他添加剂可为矿物油和植物油。
可使用着色剂,如无机颜料(例如氧化铁、氧化钛和普鲁士蓝)和有机染料(如茜素染料、偶氮染料和金属酞菁染料)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1至95%(重量),优选0.5至90%(重量)的活性化合物。
本发明的活性化合物可存在于其市售制剂和由这些制剂制得的使用形式中,例如与其他活性化合物(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质或除草剂)的混合物形式。杀虫剂包括例如特别是磷酸酯、氨基甲酸酯、羧酸酯、氯代烃、苯脲和微生物产生的物质。
本发明的活性化合物还可存在于其市售制剂和由这些制剂制得的使用形式中,例如与其他增效剂的混合物。增效剂为可提高活性化合物作用而增效剂本身不必有活性的化合物。
由市售制剂制得的使用形式的活性化合物含量可在宽的限度变化。使用形式的活性化合物浓度可为0.0000001至95%(重量)活性化合物,优选0.0001至1%(重量)。
化合物以适于使用形式的方式使用。
当用于防治卫生部门害虫和储存产品的害虫时,活性化合物表现出极优的对木材和粘土的残效作用(residual action)、以及在石灰基底上对碱的良好稳定性。
采用下列实施例进一步说明本发明式(I)化合物的制备过程。
如无另外说明,则百分比均以重量计。制备实施例
实施例1(方法a)
室温下,将15.2g(0.136mol)叔丁醇钾加到11.7g(0.131mol)O-甲基-乙羟肟酸的100ml乙腈溶液中,在室温(约20℃)下继续搅拌混合物20分钟。然后在10-15℃下滴加27.7g(0.128mol)S-叔丁基O-乙基氯代硫代磷酸酯,再在室温下继续搅拌混合物18小时。真空蒸除溶剂,残留物用300ml甲苯处理,每次用100ml水萃取总计3次。有机相经干燥,真空蒸发。残留物于60℃在高真空下进行初期蒸馏。如此得到22.2g(理论值的64%)黄色油状的S-叔丁基O-乙基O-(甲氧基亚氨基)-乙基硫代磷酸酯,折光指数nD 221.4731。
实施例2(方法b)
在-10℃,将2.7g(0.027mol)三乙胺滴加到4.8g(0.025mol)S-丙基二氯代硫代磷酸酯的30ml甲苯溶液中,然后滴加1.2g(0.026mol)乙醇。10℃下继续搅拌反应混合物3小时,然后在-10℃加入4g(0.0265mol)O-甲基苯氧肟酸、2.8g(0.028mol)三乙胺和20ml丙酮的混合物。在室温(约20℃)继续搅拌反应混合物过夜,混合物然后用20ml水洗一次,用20ml 5%(重量)盐酸洗一次,再用20ml水洗一次。有机相经干燥、真空蒸发。残留物在60℃高真空下进行初期蒸馏。这样得到4.7g(理论值的59%)黄色油状的O-乙基S-丙基O-(甲氧基亚氨基苯基)-甲基硫代磷酸酯。
以相似于实施例1和实施例2的方式,得到下列通式(I)化合物:表1实施 R R1 R2 R3 折光指数例号3 C2H5 sec-C4H9 CH3 tert-C4H9 nD 22:1.46514 C2H5 sec-C4H9 CH3 CH3-O-CH2 nD 22:1.46965 C2H5 sec-C4H9 CH3
nD 22:1.52056 n-C3H7 C2H5 CH3 tert-C4H9 nD 22:1.47117 C2H5 C2H5 CH3 tety-C4H9 nD 22:1.46538 C2H5 n-C3H7 CH3 tert-C4H9 nD 22:1.4651实施 R R1 R2 R3 折光指数例号9 n-C3H7 sec-C4H9 CH3 tert-C4H9 nD 22:1.463810 CH3 sec-C4H9 CH3 tert-C4H9 nD 22:1.465711 n-C3H7 n-C3H7 CH3 tert-C4H9 nD 22:1.463012 n-C3H7 C2H5 CH3
nD 22:1.521413 n-C3H7 sec-C4H9 CH3
nD 22:1.516214 n-C3H7 n-C3H7 CH3
nD 22:1.520315 C2H5 C2H5 CH3
nD 22:1.528416 C2H5 sec-C4H9 CH3
nD 22:1.531417 C2H5 sec-C4H9 CH3
nD 22:1.483518 C2H5 n-C3H7 CH3
nD 22:1.465219 C2H5 sec-C4H9 C2H5
实施 R R1 R2 R3 折光指数例号20 C2H5 n-C3H7 C2H5
31P NMRδ=22.776ppm21 C2H5 n-C3H7 C2H5 tert-C4H922 C2H5 n-C3H7 n-C3H7 tert-C4H923 C2H5 sec-C4H9 n-C3H7 tert-C4H924 C2H5 sec-C4H9 n-C3H7
25 C2H5 sec-C4H9 i-C3H7
26 C2H5 sec-C4H9 i-C3H7 tert-C4H927 C2H5 n-C3H7 i-C3H7 tert-C4H928 C2H5 n-C3H7 CH3 i-C3H729 C2H5 sec-C4H9 CH3 i-C3H730 C2H5 sec-C4H9 CH3 ClCH2C(CH3)2-
采用下列生物学实施例说明通式(I)化合物的生物学活性。
实施例A
辣根猿叶甲幼虫试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
将甘兰叶(Brassica oleracea)浸入所需浓度的活性化合物制剂中进行处理,在叶子仍为湿的状态期间用辣根猿叶甲幼虫(PhaedonCochleariae)进行侵扰。
经过所需时间后,确定百分破坏率。100%意味着所有辣根猿叶甲幼虫都被杀死,0%意味着没有辣根猿叶甲幼虫被杀死。
在本实验中,例如活性化合物浓度为0.01%的制备实施例3、5、9和17的化合物3天后表现出100%的破坏率。
实施例B
菜蛾试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
把甘兰叶(Brassica oleracea)浸入所需浓度的活性化合物制剂中进行处理,并在叶子仍为湿的状态时用菜蛾毛虫(Plutellamaculipennis)进行侵扰。
经过所需时间后,确定百分破坏率。100%意味着所有菜蛾毛虫都被杀死,0%意味着没有菜蛾毛虫被杀死。
在本实验中,例如活性化合物浓度为0.01%的制备实施例3、4、5、8、9、16、17和18的化合物3天后表现出100%的破坏率。实施例C黑尾叶蝉试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
把水稻苗(Oryzae sativa)浸入所需浓度的活性化合物制剂中进行处理,并在秧苗仍为湿的状态时用黑尾叶蝉幼虫(Nephotettixcincticeps)进行侵扰。
经过所需时间后,确定百分破坏率。100%表明所有黑尾叶蝉都被杀死,0%表明没有黑尾叶蝉被杀死。
在本实验中,活性化合物浓度为0.01%的制备实施例12和16的化合物6天后表现出100%的破坏率。
实施例D
桃蚜试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
被桃蚜(Myzus persicae)严重侵扰的甘兰叶(Brassica oleracea)浸入所需浓度的活性化合物制剂中进行处理。
经过所需时间后,确定百分作用情况。100%意味着所有桃蚜都被杀死,0%意味着没有桃蚜被杀死。
在本实验中,活性化合物浓度为0.01%的制备实施例5的化合物1天后表现出100%的活性。实施例E棉红螨试验(OP抗性)
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用含乳化剂的水稀释至所需浓度。
将被各种发育期的棉红螨(Tetranychus urticae)严重侵扰的豆类植物(Phaseolus vulgaris)浸入所需浓度的活性化合物制剂中进行处理。
经过所需时间后,确定百分活性。100%意味着所有棉红螨都被杀死,0%意味着没有棉红螨被杀死。
在本实验中,例如活性化合物浓度为0.1%的制备实施例5和16的化合物7天后表现出100%的活性。
实施例F临界浓度实验/线虫
实验线虫: Meloidogyne incognita
溶剂: 4份(重量)丙酮
乳化剂: 1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,浓液用水稀释到所需浓度。
将活性化合物制剂与被实验线虫严重侵扰的土壤紧密混合。活性化合物在制剂中的浓度几乎不重要。起决定作用的只是每单位体积土壤的活性化合物量,以ppm(=mg/L)表示。将处理过的土壤装入罐中,种入莴苣,将罐保持于25℃的温室温度中。
4周后,检查莴苣的线虫侵扰情况(根部光秃),用%确定活性化合物的作用程度。如果完全避免侵扰,则作用程度为100%,而如果侵扰水平和在未处理组同样侵扰的土壤中的对照植物一样高,则为0%。
在本实验中,例如活性化合物浓度为10ppm的制备实施例3和8的化合物表现出100%的作用程度。
Claims (9)
2.按权利要求1的化合物,其中
R 代表任选被卤素和/或C1-C4烷氧基取代的C1-C6
烷基;
R1代表任选被卤素和/或C1-C4烷氧基取代的C1-C6
烷基;
R2代表任选被卤素和/或C1-C4烷氧基取代的C1-C6
烷基;和
R3代表任选被卤素和/或C1-C4烷氧基取代的C1-C6
烷基、任选被卤素和/或C1-C4烷基和/或C1-C4
烷氧基取代的C3-C7环烷基,其中C1-C4烷基和
C1-C4烷氧基可被卤素取代,或者代表可含一个或多个
相同或不相同的选自下列基团的取代基的苯基:
卤素、C1-C4烷基和/或C1-C4烷氧基,其中C1-C4
烷基和C1-C4烷氧基可被卤素取代、硝基和/或氰基
(CN)。
3.按权利要求1的化合物,其中
R 代表任选被卤素和/或C1-C4烷氧基取代的C1-C4
烷基;
R1代表任选被卤素和/或C1-C4烷氧基取代的C1-C4
烷基;
R2代表任选被卤素和/或C1-C4烷氧基取代的C1-C4
烷基;和
R3代表任选被卤素和/或C1-C4烷氧基取代的C1-C5
烷基、或代表任选被卤素和/或C1-C4烷基和/或C1-C4
烷氧基取代的C3-C5环烷基,其中C1-C4烷基和
C1-C4烷氧基可被卤素取代,或代表可含一个或多个相
同或不相同的选自下列基团的取代基的苯基:
卤素、C1-C4烷基和/或C1-C4烷氧基,其中C1-C4
烷基和C1-C4烷氧基可被卤素取代、硝基和/或氰基
(CN)。
4.按权利要求1的化合物,其中
R代表C1-C4烷基;
R1代表C1-C4烷基;
R2代表C1-C4烷基;和
R3代表任选被氯和/或C1-C2烷氧基取代的C1-C5烷
基,或代表任选被氯取代的C5-C6环烷基或苯基。
6.农药,其特征在于它们含有至少一种权利要求1的通式(I)化合物。
7.权利要求1的通式(I)化合物防治害虫的应用。
8.防治害虫的方法,其特征在于使权利要求1的通式(I)化合物作用于害虫和/或害虫栖息地。
9.生产农药的方法,其特征在于使权利要求1的通式(I)化合物与稀释剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19934334196 DE4334196A1 (de) | 1993-10-07 | 1993-10-07 | Phosphorsäure-Derivate |
DEP4334196.9 | 1993-10-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1133046A true CN1133046A (zh) | 1996-10-09 |
Family
ID=6499618
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 94193706 Pending CN1133046A (zh) | 1993-10-07 | 1994-09-26 | 用作农药的硫代磷酸酯 |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0722450A1 (zh) |
JP (1) | JPH09503764A (zh) |
CN (1) | CN1133046A (zh) |
AU (1) | AU7809994A (zh) |
DE (1) | DE4334196A1 (zh) |
WO (1) | WO1995009860A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08231566A (ja) * | 1994-12-28 | 1996-09-10 | Nippon Bayeragrochem Kk | 有機燐酸エステル誘導体及び殺虫殺センチュウ剤 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2545392A1 (de) * | 1975-10-10 | 1977-04-21 | Bayer Ag | Benzimidoylthionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
JPS58222123A (ja) * | 1982-06-18 | 1983-12-23 | Yoshino Kogyosho Co Ltd | 合成樹脂製シ−ト状体 |
US4473562A (en) * | 1982-08-26 | 1984-09-25 | Chevron Research Company | Pesticidal O-(N-alkoxy-aliphatic hydroxamate)-phosphorus esters and thioesters |
JPS61133236A (ja) * | 1984-12-03 | 1986-06-20 | Showa Denko Kk | キヤツプラベル |
JPH08183495A (ja) * | 1994-12-29 | 1996-07-16 | Toshiyuki Fujiwara | 水上浮体構造物の海抜高さ制御方法 |
-
1993
- 1993-10-07 DE DE19934334196 patent/DE4334196A1/de not_active Withdrawn
-
1994
- 1994-09-26 AU AU78099/94A patent/AU7809994A/en not_active Abandoned
- 1994-09-26 WO PCT/EP1994/003203 patent/WO1995009860A1/de not_active Application Discontinuation
- 1994-09-26 CN CN 94193706 patent/CN1133046A/zh active Pending
- 1994-09-26 EP EP94928815A patent/EP0722450A1/de not_active Withdrawn
- 1994-09-26 JP JP7510588A patent/JPH09503764A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO1995009860A1 (de) | 1995-04-13 |
JPH09503764A (ja) | 1997-04-15 |
EP0722450A1 (de) | 1996-07-24 |
AU7809994A (en) | 1995-05-01 |
DE4334196A1 (de) | 1995-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1080258C (zh) | 用作农药的1-h-3-芳基-吡咯烷-2,4-二酮衍生物 | |
CN1065524C (zh) | 取代的苯乙酰胺类化合物及其中间体和其制备方法 | |
CN1017396B (zh) | 含1,2,3,6-四氢-5-硝基-嘧啶衍生物的农药组合物,其制备方法及用途 | |
CN1111623A (zh) | 新型除草的嘧啶衍生物、其制备方法及其作除草剂的用途 | |
CN1021011C (zh) | 含2,2-二氟环丙基乙烷衍生物的杀虫和杀螨剂组合物及其用途 | |
CN1073799C (zh) | 4-氯-1-(乙氧甲基)-2-(对氯苯基)-5-(三氟甲基)吡咯-3-腈的应用 | |
CN1030912A (zh) | 1-芳基吡唑 | |
CN1511142A (zh) | 吡唑酰胺衍生物及用于制备该衍生物的中间体、以该衍生物为活性成分的有害生物防治剂 | |
CN1113238A (zh) | 取代的吡唑啉衍生物 | |
CN1133046A (zh) | 用作农药的硫代磷酸酯 | |
CN86102102A (zh) | 新型苯甲酰胺的制备工艺及其用途 | |
CN1042630C (zh) | 取代的氮杂环烷烃及其制备方法、用途和含其的杀害虫组合物 | |
CN1081185C (zh) | 用作杀虫剂和杀螨剂的n-芳基硫代腙衍生物 | |
CN1086513A (zh) | 取代的2-芳基吡咯 | |
CN1052008C (zh) | 磷酸衍生物 | |
CN1057523C (zh) | 二苯基噁唑啉衍生物、制法、应用和组合物 | |
CN86102323A (zh) | 制备乙烯基环丙烷羧酸脂的方法 | |
CN1016062B (zh) | S,s-二(叔烷基)硫代膦酸酯杀虫剂 | |
CN88100536A (zh) | 2-亚氨基-1,3-二硫环丁烷类化合物及其制备方法和作为杀虫剂的应用 | |
CN86101870A (zh) | 新颖苯甲酰脲类的制备及其应用 | |
CN1259118A (zh) | 有机化合物 | |
CN1019941C (zh) | 用苯并异噻唑生物防治稻瘟病的方法 | |
CN1122330A (zh) | 吡唑衍生物、它们的制备方法及应用 | |
CN1191532A (zh) | 5,6-二氢-1,3-噁嗪类化合物的制备方法 | |
CN1244570C (zh) | 烷基黄原酸酯和它们作为农药的用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination |