CN1177345A - 氨基酸酰胺衍生物及其作为农药的应用 - Google Patents
氨基酸酰胺衍生物及其作为农药的应用 Download PDFInfo
- Publication number
- CN1177345A CN1177345A CN96192263A CN96192263A CN1177345A CN 1177345 A CN1177345 A CN 1177345A CN 96192263 A CN96192263 A CN 96192263A CN 96192263 A CN96192263 A CN 96192263A CN 1177345 A CN1177345 A CN 1177345A
- Authority
- CN
- China
- Prior art keywords
- group
- optional
- different
- ethyl
- base
- 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
- 150000001413 amino acids Chemical class 0.000 title abstract description 12
- 239000000575 pesticide Substances 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000005864 Sulphur Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- -1 aryl alkane Chemical class 0.000 claims description 335
- 239000011737 fluorine Substances 0.000 claims description 101
- 229910052731 fluorine Inorganic materials 0.000 claims description 101
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 99
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 89
- 239000000460 chlorine Substances 0.000 claims description 89
- 229910052801 chlorine Inorganic materials 0.000 claims description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 84
- 150000001721 carbon Chemical group 0.000 claims description 83
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 60
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 60
- 229910052794 bromium Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 28
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 27
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 125000001118 alkylidene group Chemical group 0.000 claims description 16
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 16
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000005023 xylyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 229950001891 iprotiazem Drugs 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- RABBMOYULJIAFU-UHFFFAOYSA-N 1h-pyrrole;thiophene Chemical class C=1C=CNC=1.C=1C=CSC=1 RABBMOYULJIAFU-UHFFFAOYSA-N 0.000 claims 3
- 230000002508 compound effect Effects 0.000 claims 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical group CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 70
- 241000894006 Bacteria Species 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000003851 azoles Chemical class 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 241000233622 Phytophthora infestans Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- 241000723353 Chrysanthemum Species 0.000 description 4
- 235000007516 Chrysanthemum Nutrition 0.000 description 4
- 241000371644 Curvularia ravenelii Species 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi 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
- 241000233679 Peronosporaceae Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
- 235000014787 Vitis vinifera Nutrition 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 229940031815 mycocide Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000003862 amino acid derivatives Chemical class 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 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 3
- 239000007789 gas Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241001157813 Cercospora Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000228437 Cochliobolus Species 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 239000005780 Fluazinam Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 241001223281 Peronospora Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- TZBPRYIIJAJUOY-UHFFFAOYSA-N Pirimiphos-ethyl Chemical group CCOP(=S)(OCC)OC1=CC(C)=NC(N(CC)CC)=N1 TZBPRYIIJAJUOY-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 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
- 241001123569 Puccinia recondita Species 0.000 description 2
- 241000228453 Pyrenophora Species 0.000 description 2
- 239000005663 Pyridaben Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000722133 Tilletia Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides 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
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 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 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 239000010903 husk Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 2
- 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 2
- 239000000463 material Substances 0.000 description 2
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 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
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 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
- 239000000843 powder Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 1
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-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
- FSJYRLHKLVGCNH-UHFFFAOYSA-N (3-tert-butylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)(C)C)=C1 FSJYRLHKLVGCNH-UHFFFAOYSA-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
- VEMKTZHHVJILDY-WOJBJXKFSA-N (5-benzylfuran-3-yl)methyl (1s,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-WOJBJXKFSA-N 0.000 description 1
- RZXVEBVXHRSQPO-UHFFFAOYSA-N (5-chloro-1,3-thiazol-2-yl)methylsulfanyl-dimethoxy-sulfanylidene-lambda5-phosphane Chemical compound COP(=S)(OC)SCc1ncc(Cl)s1 RZXVEBVXHRSQPO-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
- 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- 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
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- WHXCGIRATPOBAY-VOTSOKGWSA-N (ne)-n-hexan-2-ylidenehydroxylamine Chemical compound CCCC\C(C)=N\O WHXCGIRATPOBAY-VOTSOKGWSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-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
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- RURQAJURNPMSSK-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-{[2-(4-ethoxyphenyl)-3,3,3-trifluoropropoxy]methyl}benzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)COCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 RURQAJURNPMSSK-UHFFFAOYSA-N 0.000 description 1
- 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 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
- OZOMQRBLCMDCEG-VIZOYTHASA-N 1-[(e)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N\N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-VIZOYTHASA-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
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- KPNPDRFFWQBXGT-UHFFFAOYSA-N 1-dimethoxyphosphorylsulfanyl-2-ethylsulfanylethane;2-ethylsulfanylethoxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSCCOP(=S)(OC)OC.CCSCCSP(=O)(OC)OC KPNPDRFFWQBXGT-UHFFFAOYSA-N 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- AUQAUAIUNJIIEP-UHFFFAOYSA-N 3,4,5-trimethylphenyl methylcarbamate Chemical compound CNC(=O)OC1=CC(C)=C(C)C(C)=C1 AUQAUAIUNJIIEP-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
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- SBUKOHLFHYSZNG-UHFFFAOYSA-N 4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-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
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d 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(O[C@@H]([C@@H](C)CC4)C(C)C)O3)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.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241001149961 Alternaria brassicae Species 0.000 description 1
- 241001157812 Alternaria brassicicola Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 239000005742 Bupirimate Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- 229910021532 Calcite Inorganic materials 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
- 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
- VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical compound CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000906476 Cercospora canescens Species 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 241000760356 Chytridiomycetes Species 0.000 description 1
- PITWUHDDNUVBPT-UHFFFAOYSA-N Cloethocarb Chemical compound CNC(=O)OC1=CC=CC=C1OC(CCl)OC PITWUHDDNUVBPT-UHFFFAOYSA-N 0.000 description 1
- 239000005654 Clofentezine Substances 0.000 description 1
- 241001478240 Coccus Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- VBKKVDGJXVOLNE-UHFFFAOYSA-N Dioxation Chemical compound CCOP(=S)(OCC)SC1OCCOC1SP(=S)(OCC)OCC VBKKVDGJXVOLNE-UHFFFAOYSA-N 0.000 description 1
- MTBZIGHNGSTDJV-UHFFFAOYSA-N Ditalimfos Chemical compound C1=CC=C2C(=O)N(P(=S)(OCC)OCC)C(=O)C2=C1 MTBZIGHNGSTDJV-UHFFFAOYSA-N 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- OOTHTARUZHONSW-LCYFTJDESA-N Drazoxolon Chemical compound CC1=NOC(=O)\C1=N/NC1=CC=CC=C1Cl OOTHTARUZHONSW-LCYFTJDESA-N 0.000 description 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
- 241001063191 Elops affinis Species 0.000 description 1
- 239000005894 Emamectin Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 235000002756 Erythrina berteroana Nutrition 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- FGIWFCGDPUIBEZ-UHFFFAOYSA-N Etrimfos Chemical compound CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1 FGIWFCGDPUIBEZ-UHFFFAOYSA-N 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 241000218228 Humulus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- XRHGWAGWAHHFLF-UHFFFAOYSA-N Isazofos Chemical compound CCOP(=S)(OCC)OC=1N=C(Cl)N(C(C)C)N=1 XRHGWAGWAHHFLF-UHFFFAOYSA-N 0.000 description 1
- 241000228456 Leptosphaeria Species 0.000 description 1
- 241000228457 Leptosphaeria maculans Species 0.000 description 1
- 239000005912 Lufenuron Substances 0.000 description 1
- 241001344131 Magnaporthe grisea Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- SUYHYHLFUHHVJQ-UHFFFAOYSA-N Menazon Chemical compound COP(=S)(OC)SCC1=NC(N)=NC(N)=N1 SUYHYHLFUHHVJQ-UHFFFAOYSA-N 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- NTAHCMPOMKHKEU-AATRIKPKSA-N Methacrifos Chemical compound COC(=O)C(\C)=C\OP(=S)(OC)OC NTAHCMPOMKHKEU-AATRIKPKSA-N 0.000 description 1
- 239000005951 Methiocarb Substances 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- UDSJPFPDKCMYBD-UHFFFAOYSA-N Metsulfovax Chemical compound S1C(C)=NC(C)=C1C(=O)NC1=CC=CC=C1 UDSJPFPDKCMYBD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- JHXVRRJXCDAINK-UHFFFAOYSA-N NC(=O)N.N#CC#N Chemical compound NC(=O)N.N#CC#N JHXVRRJXCDAINK-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- VSKDLKJOZFLQQZ-UHFFFAOYSA-M O[Sn] Chemical compound O[Sn] VSKDLKJOZFLQQZ-UHFFFAOYSA-M 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- JAYZFNIOOYPIAH-UHFFFAOYSA-N Oxydeprofos Chemical compound CCS(=O)CC(C)SP(=O)(OC)OC JAYZFNIOOYPIAH-UHFFFAOYSA-N 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 241000201565 Peronospora viciae f. sp. pisi Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- NCXMLFZGDNKEPB-UHFFFAOYSA-N Pimaricin Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCC(C)OC(=O)C=CC2OC2CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 NCXMLFZGDNKEPB-UHFFFAOYSA-N 0.000 description 1
- 241001503460 Plasmodiophorida Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000219000 Populus Species 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 241001674391 Sphaerulina musiva Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 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
- 241001617088 Thanatephorus sasakii Species 0.000 description 1
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 description 1
- GNOOAFGERMHQJE-UHFFFAOYSA-N Thicyofen Chemical compound CCS(=O)C=1SC(C#N)=C(Cl)C=1C#N GNOOAFGERMHQJE-UHFFFAOYSA-N 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 241000007070 Ustilago nuda Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
- 241001251949 Xanthium sibiricum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000005870 Ziram Substances 0.000 description 1
- QSGNQELHULIMSJ-POHAHGRESA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] dimethyl phosphate Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl QSGNQELHULIMSJ-POHAHGRESA-N 0.000 description 1
- KIPLYOUQVMMOHB-MXWBXKMOSA-L [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O Chemical compound [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O KIPLYOUQVMMOHB-MXWBXKMOSA-L 0.000 description 1
- JNVCSEDACVAATK-UHFFFAOYSA-L [Ca+2].[S-]SSS[S-] Chemical compound [Ca+2].[S-]SSS[S-] JNVCSEDACVAATK-UHFFFAOYSA-L 0.000 description 1
- WHDHEVMINMZADQ-UHFFFAOYSA-N [F].N1C=CC=C1 Chemical class [F].N1C=CC=C1 WHDHEVMINMZADQ-UHFFFAOYSA-N 0.000 description 1
- HGFGGVSJWPEDPT-UHFFFAOYSA-N [P].O1C=NC=C1 Chemical compound [P].O1C=NC=C1 HGFGGVSJWPEDPT-UHFFFAOYSA-N 0.000 description 1
- ONGIWNNCSOOQGG-UHFFFAOYSA-N [P].[S].CC1=NC=CC=N1 Chemical compound [P].[S].CC1=NC=CC=N1 ONGIWNNCSOOQGG-UHFFFAOYSA-N 0.000 description 1
- WLYVRMLYUMOAHD-UHFFFAOYSA-N [P].[S].S1C=CC=C1 Chemical compound [P].[S].S1C=CC=C1 WLYVRMLYUMOAHD-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- GMAUQNJOSOMMHI-JXAWBTAJSA-N alanycarb Chemical compound CSC(\C)=N/OC(=O)N(C)SN(CCC(=O)OCC)CC1=CC=CC=C1 GMAUQNJOSOMMHI-JXAWBTAJSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940059260 amidate Drugs 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
- 238000004176 ammonification Methods 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin 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](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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 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
- 150000001540 azides Chemical class 0.000 description 1
- RQVGAIADHNPSME-UHFFFAOYSA-N azinphos-ethyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OCC)OCC)N=NC2=C1 RQVGAIADHNPSME-UHFFFAOYSA-N 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 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
- 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
- 150000001555 benzenes Chemical class 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-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
- 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
- 150000004283 biguanides Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 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
- 244000309464 bull Species 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
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- SFNPDDSJBGRXLW-UITAMQMPSA-N butocarboxim Chemical compound CNC(=O)O\N=C(\C)C(C)SC SFNPDDSJBGRXLW-UITAMQMPSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 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
- 150000001718 carbodiimides Chemical class 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 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
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- XFDJMIHUAHSGKG-UHFFFAOYSA-N chlorethoxyfos Chemical compound CCOP(=S)(OCC)OC(Cl)C(Cl)(Cl)Cl XFDJMIHUAHSGKG-UHFFFAOYSA-N 0.000 description 1
- QGTYWWGEWOBMAK-UHFFFAOYSA-N chlormephos Chemical compound CCOP(=S)(OCC)SCCl QGTYWWGEWOBMAK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WKILJWPRNQPQEX-UHFFFAOYSA-N chlorobenzene pyrimidine Chemical class N1=CN=CC=C1.ClC1=CC=CC=C1 WKILJWPRNQPQEX-UHFFFAOYSA-N 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 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
- 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
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-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
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 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
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- VEENJGZXVHKXNB-VOTSOKGWSA-N dicrotophos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)N(C)C VEENJGZXVHKXNB-VOTSOKGWSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-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
- 230000029087 digestion Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 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
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.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]([NH2+]C)[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 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 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
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 description 1
- IGUYEXXAGBDLLX-UHFFFAOYSA-N ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate Chemical compound O=C1C(C(=O)OCC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 IGUYEXXAGBDLLX-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical class CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-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
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-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
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-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
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 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
- 239000000706 filtrate Substances 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 description 1
- 229950006719 fluazuron Drugs 0.000 description 1
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- IPENDKRRWFURRE-UHFFFAOYSA-N fluoroimide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(Cl)=C(Cl)C1=O IPENDKRRWFURRE-UHFFFAOYSA-N 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-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
- 239000004088 foaming agent Substances 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
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- HAWJXYBZNNRMNO-UHFFFAOYSA-N furathiocarb Chemical compound CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 HAWJXYBZNNRMNO-UHFFFAOYSA-N 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 229930000755 gossypol Natural products 0.000 description 1
- 229950005277 gossypol Drugs 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- WIFXJBMOTMKRMM-UHFFFAOYSA-N halfenprox Chemical compound C=1C=C(OC(F)(F)Br)C=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WIFXJBMOTMKRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 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
- 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 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
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 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
- 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
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229960002418 ivermectin 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960000521 lufenuron Drugs 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
- 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
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 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
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- 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 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 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
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[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 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 description 1
- 229960004816 moxidectin Drugs 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 1
- 229960003255 natamycin Drugs 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- PZXOQEXFMJCDPG-UHFFFAOYSA-N omethoate Chemical compound CNC(=O)CSP(=O)(OC)OC PZXOQEXFMJCDPG-UHFFFAOYSA-N 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 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
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 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
- 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
- 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
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 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
- 150000003053 piperidines Chemical class 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 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
- 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
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 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
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue 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
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 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
- 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
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 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
- 235000009566 rice Nutrition 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.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](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.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](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 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
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-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
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-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
- 108010067167 thuricin Proteins 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-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
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
本发明涉及新颖的取代氨基酸酰胺,其多种制备方法和其作为农药的应用,其中A代表单键或任选取代的亚烷基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1代表各任选取代的烷基、链烯基、炔基、环烷基、环烯基、芳基烷基、芳基、杂环基烷基或杂环基,R2、R5相同或不同且各代表氢或各任选取代的烷基,R3代表氢、或代表各任选取代的烷基或环烷基,R4代表各任选取代的烷基或环烷基,或R3和R4同与之相连的碳原子一起形成任选取代的碳环,且R6代表各任选取代的环烷基、环烯基、芳基或杂环基。
Description
本发明涉及新颖的取代氨基酸酰胺、其多种制备方法和其作为农药的应用。
已知某些取代的氨基酸酰胺例如化合物N-(叔丁氧羰基)-L-缬氨酸-[N-(1-苯基乙基)-酰胺]或化合物N-(叔丁氧羰基)-L-缬氨酸-(N-[1-(2-氯苯基)乙基]-酰胺}或化合物N-(叔丁氧羰基)-L-缬氨酸-{N-甲基-N-[1-(4-氯苯基)乙基]-酰胺}具有杀真菌性能(参见例如EP 398072)。
然而,这些现有技术中的化合物的活性,特别是在低施用量和浓度下,并不是在所有的施用领域总令人满意
基、芳基、杂环基烷基或杂环基,R2、R5相同或不同且各代表氢或各任选取代的烷基,R3 代表氢,或代表各任选取代的烷基或环烷基,R4 代表各任选取代的烷基或环烷基,或R3和R4同与之相连的碳原子一起形成任选取代的碳环,且R6 代表各任选取代的环烷基、环烯基、芳基或杂环基。
在定义中,饱和或不饱和烃链,如烷基、烷二基、链烯基或炔基,包括与杂原子相连,如在烷氧基、烷硫基或烷基氨基中,各是直链或支链的。
卤素通常代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
芳基代表芳族的单或多环烃环,如苯基、萘基、蒽基或菲基,优选苯基或萘基,特别是苯基。
杂环代表饱和或不饱和的环形式的芳族化合物,其中至少一个环原子是杂原子,即不同于碳的原子。如果环含有几个杂原子,则它们可以是相同或不同。杂原子优选是氧、氮或硫。这些环形式的化合物任选与另外的碳环或杂环的稠合的或桥连的环一起形成多环体系。优选的是单或二环体系,特别是单或二环芳环体系。
环烷基代表饱和的环形式的碳环化合物,它任选与另外的碳环的、稠合或桥连的环一起形成多环体系。
环烯基代表含有至少一个双键的环形式的碳环化合物,且任选与另外的碳环的稠合或桥连的环一起形成多环。
还发现,新颖的通式(I)氨基酸酰胺可以通过如下方法获得:使通式(II)的N-取代氨基酸其中Q1、Q2、Q3、R1、R2、R3和R4各具有上述含意,如果需要在反应助剂存在下,如果需要在稀释剂存在下,与通式(III)的胺反应其中A、R5和R6具有上述含意。
最后,业已发现,新颖的通式(I)的氨基酸酰胺具有非常强的杀真菌作用。
本发明化合物任选以各种可能异构体形式的混合物形式存在,特别是立体异构体,如E和Z、苏型和赤型和光学异构体。本文描述且要求保护E和Z异构体、苏型和赤型异构体以及光学异构体和这些异构体的任意混合物。
本发明优选涉及这样的式(I)化合物,其中A 代表单键,或代表具有1至6个碳原子的亚烷基,它任选由相同或
不同的取代基单或多取代,其中可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各
具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷
基磺酰基,它们各具有1至6个碳原子和1至13个相同或不同的卤
原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
具有3至6个碳原子的环烷基;和
芳基或杂环基,它们各任选由相同或不同的下列取代基单或多取
代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或两次键连的(twice attached)亚烷基或二氧亚烷基,它们各具
有1至6个碳原子且任选由相同或不同的下列取代基单或多取代:
卤素和/或具有1至4个碳原子的直链或支链烷基和/或具有1至4个
碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表具有1至8个碳原子的烷基,它任选由相同或不同的下列取代
基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-C4-
烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基(它们各可由卤
素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至7个碳原子的环烷基或环烯基,它们各任选由下列
相同或不同的取代基单或多取代:卤素、氰基、羧基、苯基(它任选
由卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或
C1-C4-卤代烷氧基取代)、C1-C4-烷基或C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基、芳烷基或杂环基,它们各任选
由相同或不同的取代基单或多取代,其中可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
二次键连的亚烷基或二氧亚烷基,它们具有1至6个碳原子,各任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或二次键连的亚烷基或二氧基亚烷基,它们各具有1至6个碳原
子,任选由相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。R2、R3相同或不同且各代表氢,或代表具有1至4个碳原子的烷基或
具有3至6个碳原子的环烷基,它们各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代)R3 代表氢,或代表具有1至8个碳原子的烷基,它各任选由相同或不
同的取代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、
C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各
任选由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代
烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;R4 代表具有1至8个碳原子的烷基,它各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代
烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;或R3和R4同与之相连的碳原子一起形成具有3至8个碳原子的碳环,该
碳环任选由相同或不同的下列取代基单或多取代:卤素、氰基、羟
基、氨基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-
烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选由卤素取代)且R6 代表具有3至8个碳原子的环烷基或环烯基,它们任选由相同或不
同的下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤
素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-
卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基或杂环基,它们各任选由相同或
不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
二次键连的亚烷基或二氧亚烷基,它们各具有1至6个碳原子且任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基;
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基;
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基;
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基;
和/或二次键连的亚烷基或二氧基亚烷基,它们各具有1至6个碳原
子且任选各由相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。
本发明特别涉及这样的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、1-、2-、3-、
新戊基、1-、2-、3-、4-(2-甲基丁基)、1-、2-、3-己基、1-、2-、
3-、4-、5-(2-甲基戊基)、1-、2-、3-、(3-甲基戊基)、2-乙基丁基、
1-、3-、4-(2,2-二甲基丁基)、1-、2-(2,3-二甲基丁基),它们任选由
下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧基、
乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰
基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、甲氧基、乙氧基、氰基、羧基、苯基(它
任选由氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧
基或三氟甲氧基取代)、甲基、乙基、正或异丙基、甲氧羰基或乙氧
羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连两
次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基,
环丙基、环丁基、环戊基或环己基;R2、R5相同或不同且各代表氢、或代表甲基、乙基、正或异丙基、或
正、异、仲或叔丁基,R3 代表氢,或代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,或R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连二次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它
们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
特别优选的是这样的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们任选由
下列取代基单至三取代:氟、氯、溴、甲氧基、乙氧基、甲硫基、
乙硫基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟或氯单至三取代;
或代表环丁基、环戊基或环己基,它们各任选由下列取代基单至六
取代:氟、氯、溴、甲氧基、乙氧基、苯基(它任选由氟、氯、溴、
氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、
甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代)、
甲基、乙基、正或异丙基;
或代表苯基、萘基、苄基、呋喃基、苯并呋喃基、噻吩基、苯并噻
吩基、吡啶基、喹啉基、四氢呋喃基、全氢吡喃基,它们各任选单
至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正
或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、
三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、
三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基
亚磺酰基或三氟甲磺酰基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、
乙氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、
甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧
基亚氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各键连两次
且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基,R2、R5相同或不同且各代表氢、或代表甲基,R3 代表氢,或代表甲基、乙基,正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连二次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它
们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
非常特别优选的本发明式(I)化合物是这样的一组化合物,其中A 代表单键或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙基、
1,2-亚丙基或2,2-亚丙基,Q1、Q2、Q3各代表氧,R1 代表甲基、乙基、正或异丙基、正、并、仲或叔丁基、 环戊基、环
己基或代表任选由甲基、乙基、甲氧基、乙氧基、溴、氯或氟取代
的苯基或苄基,R2、R5各代表氢,R3 代表氢、甲基、乙基或环丙基,R4 代表甲基、乙基或环丙基,或R3和R4同与之相连的碳原子一起形成环戊烷环或环己烷环,且R6 代表环己基,它各任选由甲基、乙基、甲氧基或乙氧基单或二取代;
或代表苯基、萘基、呋喃基、苯并呋喃基、吡咯基、吲哚基、噻吩
基、苯并噻吩基、吡啶基、喹啉基、嘧啶基、哒嗪基、吡嗪基,它
们各任选单至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲基
氨基、二乙基氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧
羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧
基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚
氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连两
次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基。
所给的上述一般或优选基团定义适合于式(I)终产物,且相应地适合于在每种制备情况下所需的原料或中间体。
这些基团定义可以按需要相互组合,优选化合物所述范围间的组合也是可能的。
式(II)提供进行本发明方法所需的原料氨基酸的一般定义。在此式(II)中,Q1、Q2、Q3、R1、R2、R3和R4各优选或特别是具有与本发明式(I)化合物描述相关的定义中已经给出的优选或特别优选的Q1、Q2、Q3、R1、R2、R3和R4的含意。
式(II)的原料是已知的和/或可以通过已知的方法制备(参见例如Shin,Chung,Gi等人《化学药物公报》(Chem.Pharm.Bull.)1984,3934-3944)。
式(III)提供进行本发明方法所需的另一种原料胺的一般定义。在此式(III)中,A、R5和R6优选或特别是具有与本发明式(I)化合物描述相关的定义中已经给出的优选或特别优选的A、R5和R6的含意。
式(III)的胺是有机化学已知的试剂。
如果需要,本发明的方法在稀释剂存在下进行。进行本发明方法的适合的稀释剂是所有的惰性有机溶剂。这些溶剂包括特别是脂族、脂环族或芳族烃类,如,石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘,卤代烃类,如,氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如,乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;酮类,如,丙酮、丁酮、甲基异丁基酮或环己酮;腈类,如,乙腈、丙腈、正或异丁腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如,乙酸甲酯或乙酸乙酯;亚砜类,如二甲亚砜;砜类如环丁砜。
如果需要,本发明是在适合的缩合剂存在下进行的。可能的缩合剂是所有的通常可以用于这种酰胺化反应的缩合剂。形成酰基卤的试剂实例有,例如,光气、三溴化磷、三氯化磷、五氯化磷、磷酰氯或亚硫酰二氯;形成酸酐的试剂是例如,氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;碳化二亚胺,如N,N’-二环己基碳化二亚胺(DCC)、或其它常规缩合剂,如五氧化磷、多磷酸、N,N’-羰基二咪唑、2-乙氧基-N-乙氧羰基-1,2-二氢喹啉(EEDQ)或三苯基膦/四氯化碳。
如果需要,本发明的方法是在适用的酸受体存在进行的。适合的酸受体是所有的常规无机或有机碱。这些碱包括例如:碱金属或碱土金属氢化物、氢氧化物、氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一碳烯(DBU)。
如果需要,本发明方法是在催化剂存在下进行的。实例包括例如4-二甲基氨基吡啶、1-羟基苯并三唑和二甲基甲酰胺。
进行本发明方法时,反应温度可以在相当宽的范围内变化。一般而言,温度是在-78℃和+120℃之间,优选采用-60℃至+25℃间的温度。
实施本发明方法制备式(I)化合物时,每摩尔式(II)氨基酸衍生物,一般采用0.5至5摩尔,优选采用等摩尔的式(III)胺。
反应的进行以及反应产物的收集和分离是通过已知的方法来完成的(参见例如制备实施例)。
本发明的方法也可以分二个阶段进行。在这种情况下,首先将通式(II)的氨基酸衍生物转化成活化的形式,并在随后的步骤中,与通式(III)的胺反应,给出本发明通式(I)的氨基酸酰胺。
式(II)氨基酸衍生物的适合活化形式是所有的羧基活化衍生物,如酰基卤,优选酰基氯,酰基叠氮以及对称或混合的酸酐,如混合的O-烷基羧酸酐,和活化的酯,如对硝基苯基酯或N-羟基琥珀酰亚胺酯,以及与缩合剂如二环己基碳化二亚胺的加合物,或原位产生的氨基酸活化形式。
实施两步法,优选的是使用相应于式(II)氨基酸的酰基氯和混合酸酐。它们可以通过以常规的方式使式(11)的氨基酸或其盐与卤化剂或制备混合酸酐的已知试剂反应来制备,如例如五氯化磷、亚硫酰二氯、草酰氯或氯甲酸酯。
如果需要,两步法中的每一步是在稀释剂存在下,如果需要是在催化剂存在下进行的。优选的稀释剂和催化剂是那些已经提到的与一步法的描述相关的稀释剂和催化剂。
反应的进行以及反应产物的收集和分离是通过已知的方法来完成的。
本发明的活性化合物具有强的杀微生物活性,且可以实际上用来防治有害微生物。本发明活性化合物适合用作作物保护剂,特别是杀真菌剂。
杀真菌剂用在作物保护中,用于防治根肿菌纲,卵菌纲,壶菌纲,接合菌纲,子囊菌纲,担子菌纲和半知菌类。
上面列出的某些病原真菌病害以属名给出, 可以提到的有例如下列,但决不限于此:腐霉属,如终极腐霉(Pythium ultimum);疫霉属,如蔓延疫霉(Phytophthora infestans);假霜霉属,如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);单轴霉属,如葡萄生单轴霉(Plasmopara viticola);霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);白粉菌属,如禾白粉菌(Erysiphe graminis);单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);黑星菌属,如苹果黑星菌(Venturia inaequalis);核腔菌属, 如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pgrammea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);柄锈属,如隐匿柄锈菌(Puccinia recondita);腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);梨孢菌属,如稻梨孢菌(Pvricularia oryzae);镰孢属,如大刀镰孢(Fusarium culmorum);葡萄孢属,如灰色葡萄孢(Botrytis cinerea);壳针孢属,如颖枯壳针孢(Septoria nodorum);小球腔菌属,如颍枯病小球腔菌(Leptosphaeria nodorum);尾孢属,如变灰尾孢菌(Cercospora canescens);链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和假小尾孢菌属,如麦类眼斑病菌(Pseudocercosporalla herpotrichoides)。
在防治植物病害所需浓度下,植物对活性化合物的良好耐药性,使活性化合物可以处理植物的地上部分、繁殖根茎和种子以及土壤。
本发明的活性化合物可以特别成功地用于防治葡萄、果树栽培和园艺中的病害,如防治单轴霉和疫霉菌属种类引起的病害。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂、聚合物中的细微胶囊和转化成种子包衣组合物、以及ULV冷和热雾剂。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂(即液体溶剂、压力下的液化气体)混合,和/或与固体载体混合,并任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)。用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,以及水;液化气填充剂或载体是指环境温度和大气压力下是气体的液体,例如气雾抛射剂,例如卤代烃类,或丁烷、丙烷、氮气和二氧化碳; 固体载体适合的有:磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;乳化剂和/或起泡剂适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白质水解产物;分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素
制剂中可以使用粘合剂,如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,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,和合成磷脂。其它的粘合剂可以是矿物油和植物油。
也可能使用染料,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,和微量营养素如铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
当用于植物保护时,本发明的活性化合物可以其本身或以其制剂形式,与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以扩大作用谱,或为防止抗性的逐步建立。
在许多情况下,可以获得增效作用。
适合用于混合物的组分是例如下列化合物:杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺; 8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异 唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、perfurazoat、戊菌唑、戊菌隆、稻病磷、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、齐墩螨素(avermectin)、AZ 60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA 157 419、CGA 184699、除线威、chlorethoxyfos、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氧氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、fipronil、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氰虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、NI 25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、pyrachlophos、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、tebufenpyrad、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、zetamethrin。
本发明活性化合物也可与其它已知活性化合物如除草剂、或与化肥和生长调节剂混合。
活性化合物可以以其原样或以其制剂或由其制备的使用形式使用,所述的制备使用形式有例如可直接使用溶液、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾、撒施、喷粉、起泡、涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可处理植物的种子。
处理植物部分时,使用形式中的活性化合物浓度可在大范围内变化:通常,在按重量计1和0.0001%之间,优选在按重量计0.5和0.001%间使用。
处理种子时,通常每公斤种子需要0.001至50g,优选0.01至10g量的活性化合物。
处理土壤时,在作用点需要活性化合物的浓度为按重量计0.00001至0.1%,优选按重量计0.0001至0.02%。
在-20℃,将0.5g(0.005mol)N-甲基哌啶加入、之后在-20℃搅拌下将0.7g(0.005mol)氯甲酸异丁酯滴加入含1.0g(0.005mol)2-(异丙氧羰基氨基)-丁-2-烯酸的10ml二氯甲烷中。添加完毕后,在-20℃下继续搅拌10分钟,加入0.75g(0.005mol)的1-(4-甲氧基苯基)-乙胺,将温度保持在低于-15℃。之后在-15℃再搅拌2小时,并在室温下搅拌15小时,滤出沉淀出的固体物,并用二氯甲烷洗涤,滤液在减压下浓缩,残留物用水消化,并重复用乙酸乙酯萃取,合并的有机相用碳酸氢钠水溶液和水洗涤,并经硫酸钠干燥,在减压下去除溶剂,获得0.8g(理论值的47%)的N-[1-(4-甲氧基苯基)-乙基]-2-(异丙氧羰基氨基)-丁-2-烯酸酰胺,为无色油状物。1H-NMR(CDCl3,TMS):δ(ppm):1.25(m,6H)、1.50(d,3H)、1.74(d,3H)、3.79(s,3H)。表1:表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)*) 1H-NMR谱是采用四甲基硅烷作内标在氘氯仿(CDCl3)或六氘二甲基亚砜(DMSO-d)中记录的。所述的值是化学位移值,为以ppm计的d值。用途实施例实施例A葡萄生单轴霉病保护性防治试验溶剂:4.7份重量的丙酮乳化剂:0.3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用活性化合物制剂喷雾。喷液层变干后,将植株用葡萄生单轴霉病菌(Plasmopara viticola)的孢子水悬浮液接种。之后,将植株放在20-22℃和100%相对湿度的培养箱中1天。接着将植物放置于21℃和约90%相对湿度的温室中。再将植物在培养箱中湿润和放置1天。
接种6天后进行评价。
在此试验中,在活性化合物浓度为100ppm的情况下,显示大于90%效力的有例如化合物(2)、(8)、(10)、(11)、(12)、(15)、(19)、(20)、(23)、(36)、(39)和(41)。实施例B马铃薯蔓延疫霉病保护性防治试验溶剂:12.5份重量的丙酮乳化剂:0.3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用活性化合物制剂喷雾至喷雾液向下滴流。喷液层变干后,将植株用蔓延疫霉(Phytophthora infestans)的孢子水悬浮液接种。
之后,将植物放置于约20℃和100%相对湿度的培养箱中。
接种4天后进行评价。
在此试验中,在活性化合物浓度为0.05%的情况下,显示100%效力的有例如制备实施例的化合物(2)。
Claims (9)
2.根据权利要求1的式(1)化合物,其中A 代表单键,或代表具有1至6个碳原子的亚烷基,它任选由相同或
不同的取代基单或多取代,可能的取代基优选选自下列:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各
具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷
基磺酰基,它们各具有1至6个碳原子和1至13个相同或不同的卤
原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子:
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
具有3至6个碳原子的环烷基;和
芳基或杂环基,它们各任选由相同或不同的下列取代基单或多取
代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子
且任选由相同或不同的下列取代基单或多取代:卤素和/或具有1至
4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个
相同或不同卤原子的直链或支链卤代烷基;Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表具有1至8个碳原子的烷基,它任选由相同或不同的下列取代
基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-C4-
烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基(它们各可由卤
素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至7个碳原子的环烷基或环烯基,它们各任选由下列
相同或不同的取代基单或多取代:卤素、氰基、羧基、苯基(它任选
由卤素、氰基、C1-C4烷基、C1-C4-卤代烷基、C1-C4-烷氧基或
C1-C4-卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基、芳烷基或杂环基,它们各任选
由相同或不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
键连二次的亚烷基或二氧亚烷基,它们具有1至6个碳原子,且各
任选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4
个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相
同或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;
和芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂
环基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂
环基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原
子,且任选由相同或不同的下列取代基单或多取代:卤素和/或具有
1至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至
9个相同或不同卤原子的直链或支链卤代烷基,R2、R5相同或不同且各代表氢,或代表具有1至4个碳原子的烷基或
具有3至6个碳原子的环烷基,它们各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代)R3 代表氢,或代表具有1至8个碳原子的烷基,它各任选由相同或不
同的取代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、
C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各
任选由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤
代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;R4 代表具有1至8个碳原子的烷基,它各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤
代烷氧基取代)、C1-C4-烷基或C1-C4-烷氧羰基;或R3和R4同与之相连的碳原子一起形成具有3至8个碳原子的碳环,该
碳环任选由相同或不同的下列取代基单或多取代:卤素、氰基、羟
基、氨基、C1-C4烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-
烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选由卤素取代),且R6 代表具有3至8个碳原子的环烷基或环烯基,它们任选由相同或不
同的下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤
素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-
卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基或杂环基,它们各任选由相同或
不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子且任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子
且任选各被相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。
3 根据权利要求1的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、1-、2-、3-、
新戊基、1-、2-、3-、4-(2-甲基丁基)、1-、2-、3-己基、1-、
2-、3-、4-、5-(2-甲基戊基)、1-、2-、3-、(3-甲基戊基)、2-乙基
丁基、1-、3-、4-(2,2-二甲基丁基)、1-、2-(2,3-二甲基丁基),它
们任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、
甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、
甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、甲氧基、乙氧基、氰基、羧基、苯基(它
任选由氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧
基或三氟甲氧基取代)、甲基、乙基、正或异丙基、甲氧羰基或乙氧
羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连
两次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲
基、三氟甲基、乙基或正或异丙基,
环丙基、环丁基、环戊基或环己基;R2、R3相同或不同且各代表氢、或代表甲基、乙基、正或异丙基、或
正、异、仲或叔丁基,R3 代表氢,或代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,或R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
引哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
4.根据权利要求1的式(1)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们任选由
下列取代基单至三取代:氟、氯、溴、甲氧基、乙氧基、甲硫基、
乙硫基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟或氯单至三取代;
或代表环丁基、环戊基或环己基,它们各任选由下列取代基单至六
取代:氟、氯、溴、甲氧基、乙氧基、苯基(它任选由氟、氯、溴、
氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、
甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代)、
甲基、乙基、正或异丙基;
或代表苯基、萘基、苄基、呋喃基、苯并呋喃基、噻吩基、苯并噻
吩基、吡啶基、喹啉基、四氢呋喃基、全氢吡喃基,它们各任选单
至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正
或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、
三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、
三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基
亚磺酰基或三氟甲磺酰基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、
乙氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、
甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧
基亚氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连
两次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲
基、三氟甲基、乙基或正或异丙基,R2、R5相同或不同且各代表氢、或代表甲基,R3 代表氢,或代表甲基、乙基,正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
5.根据权利要求1的式(I)化合物,其中A 代表单键或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙基、
1,2-亚丙基或2,2-亚丙基,Q1、Q2、Q3各代表氧,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环戊基、
环己基或代表任选由甲基、乙基、甲氧基、乙氧基、溴、氯或氟取
代的苯基或苄基,R2、R5各代表氢,R3 代表氢、甲基、乙基或环丙基,R4 代表甲基、乙基或环丙基,或R3和R4同与之相连的碳原子一起形成环戊烷环或环己烷环,且R6 代表环己基,它各任选由甲基、乙基、甲氧基或乙氧基单或二取代;
或代表苯基、萘基、呋喃基、苯并呋喃基、吡咯基、吲哚基、噻吩
基、苯并噻吩基、吡啶基、喹啉基、嘧啶基、哒嗪基、吡嗪基,它
们各任选单至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基。
6.一种农药,其特征在于,它含有至少一种根据权利要求1的式(I)化合物。
7.防治有害生物的方法,其特征在于,使权利要求1的式(I)化合物作用于有害生物和/或其栖息地。
8.根据权利要求1至5的式(I)化合物防治有害生物的应用。
9.制备农药的方法,其特征在于,将权利要求1至5的式(I)化合物与填充剂和/或表面活性剂混合。
10.制备权利要求1的式(I)化合物的方法,其特征在于,使通式(II)的N-取代氨基酸其中Q1、Q2、Q3、R1、R2、R3和R4各具有权利要求1中所定义的含意,如果需要在反应助剂存在下,如果需要在稀释剂存在下,与通式(III)的胺反应其中A、R5和R6各具有权利要求1中所定义的含意。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19501841A DE19501841A1 (de) | 1995-01-23 | 1995-01-23 | Aminosäureamide |
DE19501841.9 | 1995-01-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1177345A true CN1177345A (zh) | 1998-03-25 |
Family
ID=7752047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96192263A Pending CN1177345A (zh) | 1995-01-23 | 1996-01-10 | 氨基酸酰胺衍生物及其作为农药的应用 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5935979A (zh) |
EP (1) | EP0805798B1 (zh) |
JP (1) | JPH10512574A (zh) |
CN (1) | CN1177345A (zh) |
AU (1) | AU4485296A (zh) |
DE (2) | DE19501841A1 (zh) |
ES (1) | ES2143176T3 (zh) |
PL (1) | PL321454A1 (zh) |
WO (1) | WO1996022970A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102020592A (zh) * | 2010-11-26 | 2011-04-20 | 湖南科技大学 | 具有杀菌活性的氨基甲酸脲甲基取代芳基酯 |
CN106508936A (zh) * | 2015-09-15 | 2017-03-22 | 南京华洲药业有限公司 | 一种含苯噻菌胺和多菌灵的杀菌组合物及其应用 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2360740A1 (en) | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63122659A (ja) * | 1986-11-13 | 1988-05-26 | S K I Baitsu Kk | α,β−デヒドロ−α−アミノ酸残基を有する特定物質の製造方法 |
DE3915755A1 (de) * | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
DE3936298A1 (de) * | 1989-11-01 | 1991-05-02 | Bayer Ag | Substituierte aminosaeureamid-derivate deren herstellung und verwendung |
DE4203084A1 (de) * | 1992-02-04 | 1993-08-05 | Bayer Ag | Substituierte aminosaeureamide |
-
1995
- 1995-01-23 DE DE19501841A patent/DE19501841A1/de not_active Withdrawn
-
1996
- 1996-01-10 CN CN96192263A patent/CN1177345A/zh active Pending
- 1996-01-10 EP EP96900932A patent/EP0805798B1/de not_active Expired - Lifetime
- 1996-01-10 JP JP8522576A patent/JPH10512574A/ja active Pending
- 1996-01-10 PL PL96321454A patent/PL321454A1/xx unknown
- 1996-01-10 DE DE59604115T patent/DE59604115D1/de not_active Expired - Fee Related
- 1996-01-10 ES ES96900932T patent/ES2143176T3/es not_active Expired - Lifetime
- 1996-01-10 AU AU44852/96A patent/AU4485296A/en not_active Abandoned
- 1996-01-10 US US08/875,035 patent/US5935979A/en not_active Expired - Fee Related
- 1996-01-10 WO PCT/EP1996/000071 patent/WO1996022970A1/de active IP Right Grant
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102020592A (zh) * | 2010-11-26 | 2011-04-20 | 湖南科技大学 | 具有杀菌活性的氨基甲酸脲甲基取代芳基酯 |
CN106508936A (zh) * | 2015-09-15 | 2017-03-22 | 南京华洲药业有限公司 | 一种含苯噻菌胺和多菌灵的杀菌组合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
PL321454A1 (en) | 1997-12-08 |
WO1996022970A1 (de) | 1996-08-01 |
DE19501841A1 (de) | 1996-07-25 |
JPH10512574A (ja) | 1998-12-02 |
EP0805798A1 (de) | 1997-11-12 |
DE59604115D1 (de) | 2000-02-10 |
AU4485296A (en) | 1996-08-14 |
ES2143176T3 (es) | 2000-05-01 |
US5935979A (en) | 1999-08-10 |
EP0805798B1 (de) | 2000-01-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1057762C (zh) | 取代的氮杂二氧杂环烯及作为杀真菌剂的应用 | |
CN1146550C (zh) | 卤代嘧啶类及其作为减少寄生虫方法的应用 | |
CN1346826A (zh) | 杀微生物卤代苯并咪唑、组合物及制备方法 | |
CN1102149C (zh) | 4-卤烷基-3-杂环基吡啶类及4-卤烷基-5-杂环基嘧啶类化合物,其制法,含其的组合物及其用作杀虫剂的用途 | |
CN1167683C (zh) | 芳基吡唑化合物、其制备方法、含其的农药组合物及其用途 | |
CN1078204C (zh) | 氨基酸酰胺衍生物及其杀真菌的用途和制备方法 | |
CN1265111A (zh) | 三唑啉硫酮磷酸衍生物 | |
CN1064957C (zh) | 用作杀微生物剂的n-磺酰和n-亚磺酰氨基酸酰胺 | |
CN1090848A (zh) | 噁二唑和噻二唑衍生物 | |
CN1231480C (zh) | 1,2,3-噻二唑羧酸(硫)酯及其作为防治害虫剂和杀微生物剂的用途 | |
CN1213050C (zh) | 氧杂双环[2.2.1]庚烷衍生物,其制备方法和作为农药的用途 | |
CN1112849C (zh) | 1,2,3-噻二唑羧酸(硫代)酯防治害物的用途 | |
CN1278804A (zh) | 异噻唑羧酸衍生物 | |
CN1065242C (zh) | 吡啶基-噻唑 | |
CN1066724C (zh) | 取代的芳基氮杂二氧杂环烯杀真菌剂 | |
CN1420875A (zh) | 异噻唑甲酸衍生物及其作为杀菌剂的应用 | |
CN1267301A (zh) | 用作农药的甲氧基亚氨基甲基噁二嗪类化合物 | |
CN1803798A (zh) | 制备杀真菌组合物的方法 | |
CN1177345A (zh) | 氨基酸酰胺衍生物及其作为农药的应用 | |
CN1181076A (zh) | 杀真菌的氮杂-杂环烯类 | |
CN1193317A (zh) | 羧酸胺衍生物及其作为农药使用 | |
CN1226235A (zh) | 巯基-咪唑基衍生物及其作为杀微生物剂的用途 | |
CN1228076A (zh) | 二芳基乙炔酮类化合物 | |
CN1134698A (zh) | 新颖的三唑化合物,其制备方法和作病虫害防治剂 | |
CN1037143A (zh) | N-苯基苯甲酰胺类和n-苯基苄胺肟类,其制备方法,含有这二类化合物的制剂及其用作杀虫剂的用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C01 | Deemed withdrawal of patent application (patent law 1993) | ||
WD01 | Invention patent application deemed withdrawn after publication |