SK154398A3 - 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents - Google Patents

1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents Download PDF

Info

Publication number: SK154398A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; optionally substituted; combination; halogen
Prior art date: 1997-11-12

Application number

SK1543-98A

Other languages

English (en)

Slovak (sk)

Inventor

Terence J Bentley

Keith D Barnes

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1997-11-12

Filing date

1998-11-09

Publication date

1999-07-12

1998-11-09 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1999-07-12 Publication of SK154398A3 publication Critical patent/SK154398A3/sk

Links

230000000895 acaricidal effect Effects 0.000 title description 10
230000000749 insecticidal effect Effects 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 73
238000000034 method Methods 0.000 claims abstract description 31
241000238631 Hexapoda Species 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 23
241000607479 Yersinia pestis Species 0.000 claims abstract description 7
-1 C 1 -C 4 alkyl Chemical group 0.000 claims description 75
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 73
125000001424 substituent group Chemical group 0.000 claims description 64
229910052736 halogen Inorganic materials 0.000 claims description 60
150000002367 halogens Chemical group 0.000 claims description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 22
125000004438 haloalkoxy group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
241000238876 Acari Species 0.000 claims description 13
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 11
206010061217 Infestation Diseases 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 7
239000002689 soil Substances 0.000 claims description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
PYCGZSRXZNSODI-UHFFFAOYSA-N 1-[4,5-difluoro-2-methyl-6-(3-phenoxyphenyl)hex-4-en-3-yl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(C)C)C(F)=C(F)CC1=CC=CC(OC=2C=CC=CC=2)=C1 PYCGZSRXZNSODI-UHFFFAOYSA-N 0.000 claims description 5
HSDKRVXUDFEKJT-UHFFFAOYSA-N 1-chloro-4-[4,5-difluoro-2-methyl-6-(3-phenoxyphenyl)hex-4-en-3-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 HSDKRVXUDFEKJT-UHFFFAOYSA-N 0.000 claims description 5
SRHYZZBUIPFLAC-UHFFFAOYSA-N 4-[2,3-difluoro-4-(4-fluorophenyl)-5-methylhex-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(F)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 SRHYZZBUIPFLAC-UHFFFAOYSA-N 0.000 claims description 5
GESXBHHYNJGUJH-UHFFFAOYSA-N 4-[2,3-difluoro-5-methyl-4-[4-(trifluoromethoxy)phenyl]hex-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 GESXBHHYNJGUJH-UHFFFAOYSA-N 0.000 claims description 5
ZKWKQYMRFFQLLV-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-2,3-difluoro-5-methylhex-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 ZKWKQYMRFFQLLV-UHFFFAOYSA-N 0.000 claims description 5
CJBOQVDSWBIJGD-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-2,3-difluoro-5-methylhex-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(C)C)C(F)=C(F)CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 CJBOQVDSWBIJGD-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
CXFIQGCANAKQCR-UHFFFAOYSA-N 1-[2,3-difluoro-4-(4-fluorophenyl)-5-methylhex-2-enyl]-3-phenoxybenzene Chemical compound C=1C=C(F)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 CXFIQGCANAKQCR-UHFFFAOYSA-N 0.000 claims description 4
GIGOGZZZIVTLIY-UHFFFAOYSA-N 1-[4,5-difluoro-2-methyl-6-(3-phenoxyphenyl)hex-4-en-3-yl]-4-(trifluoromethoxy)benzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 GIGOGZZZIVTLIY-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
235000010755 mineral Nutrition 0.000 claims description 3
239000011592 zinc chloride Substances 0.000 claims description 3
235000005074 zinc chloride Nutrition 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims description 2
150000008366 benzophenones Chemical group 0.000 claims description 2
125000006267 biphenyl group Chemical group 0.000 claims description 2
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
239000001963 growth medium Substances 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
230000000361 pesticidal effect Effects 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 27
239000003921 oil Substances 0.000 description 23
239000000243 solution Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
241000196324 Embryophyta Species 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000010183 spectrum analysis Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000000284 extract Substances 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical class BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
241001124076 Aphididae Species 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
201000002266 mite infestation Diseases 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
FTYGOBYFTGEYNF-UHFFFAOYSA-N 1-(1-bromo-2-methylpropyl)-4-chlorobenzene Chemical compound CC(C)C(Br)C1=CC=C(Cl)C=C1 FTYGOBYFTGEYNF-UHFFFAOYSA-N 0.000 description 3
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
241000489947 Diabrotica virgifera virgifera Species 0.000 description 3
241000256257 Heliothis Species 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
IFKCXNOONQSOEG-UHFFFAOYSA-N 1-chloro-4-(1,1,2-trifluoro-4-methylpent-1-en-3-yl)benzene Chemical compound FC(F)=C(F)C(C(C)C)C1=CC=C(Cl)C=C1 IFKCXNOONQSOEG-UHFFFAOYSA-N 0.000 description 2
RURVGRMAYYDRBG-UHFFFAOYSA-N 1-chloro-4-(1,2-difluoro-4-methylpent-1-en-3-yl)benzene Chemical compound FC=C(F)C(C(C)C)C1=CC=C(Cl)C=C1 RURVGRMAYYDRBG-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
WDCQSLAKMUKPSC-UHFFFAOYSA-N 4-[4,5-difluoro-2-methyl-6-(3-phenoxyphenyl)hex-4-en-3-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C(C)C)C(F)=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 WDCQSLAKMUKPSC-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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240000007124 Brassica oleracea Species 0.000 description 2
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235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
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238000004364 calculation method Methods 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
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238000009472 formulation Methods 0.000 description 2
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239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
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238000005507 spraying Methods 0.000 description 2
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238000000023 Kugelrohr distillation Methods 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
244000061458 Solanum melongena Species 0.000 description 1
235000002597 Solanum melongena Nutrition 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical class [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001499 aryl bromides Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000010974 bronze Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000004571 lime Substances 0.000 description 1
229940087305 limonene Drugs 0.000 description 1
235000001510 limonene Nutrition 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
239000004530 micro-emulsion Substances 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000000123 paper Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
HXTSPGYEPSIZKP-UHFFFAOYSA-N phenol;tin Chemical class [Sn].OC1=CC=CC=C1 HXTSPGYEPSIZKP-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000008654 plant damage Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)

SK1543-98A 1997-11-12 1998-11-09 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents SK154398A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US96905697A	1997-11-12	1997-11-12

Publications (1)

Publication Number	Publication Date
SK154398A3 true SK154398A3 (en)	1999-07-12

Family

ID=25515114

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1543-98A SK154398A3 (en)	1997-11-12	1998-11-09	1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents

Country Status (28)

Country	Link
EP (1)	EP0916640B1 (de)
JP (1)	JPH11228476A (de)
KR (1)	KR19990045151A (de)
CN (1)	CN1131191C (de)
AR (1)	AR016677A1 (de)
AT (1)	ATE219042T1 (de)
AU (1)	AU745695B2 (de)
BG (1)	BG102904A (de)
BR (1)	BR9804586A (de)
CA (1)	CA2253324A1 (de)
CO (1)	CO5040065A1 (de)
CZ (1)	CZ358798A3 (de)
DE (1)	DE69805935T2 (de)
EA (1)	EA001751B1 (de)
ES (1)	ES2178812T3 (de)
GE (1)	GEP20012507B (de)
HU (1)	HUP9802620A1 (de)
ID (1)	ID21253A (de)
IL (1)	IL126930A0 (de)
NO (1)	NO985261L (de)
NZ (1)	NZ332755A (de)
PL (1)	PL329634A1 (de)
SG (1)	SG73582A1 (de)
SK (1)	SK154398A3 (de)
TR (1)	TR199802286A2 (de)
TW (1)	TW467889B (de)
YU (1)	YU51198A (de)
ZA (1)	ZA9810321B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1351913A2 (de) *	2000-09-12	2003-10-15	Basf Aktiengesellschaft	1,4-diaryl-2,3-difluor-2-buten insectizide und akarizide mittel
CN109336733A (zh) *	2018-10-26	2019-02-15	江苏七洲绿色化工股份有限公司	一种氟环唑中间体及氟环唑的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5248834A (en) *	1984-04-09	1993-09-28	British Technology Group Limited	Pesticides
GB9219612D0 (en) *	1992-09-16	1992-10-28	Khambay Bhupinder P S	Pesticidal fluoroolefins
GB9408605D0 (en) *	1994-04-29	1994-06-22	British Tech Group	Pesticidal fluoroolefins
GB9522144D0 (en) *	1995-10-30	1996-01-03	British Tech Group	Control of whitefly
DK0811593T3 (da) *	1996-06-03	2002-09-02	Basf Ag	1,4-diaryl-2-flour-2-buten som insektcider og acaricider

1998
- 1998-10-27 TW TW087117791A patent/TW467889B/zh not_active IP Right Cessation
- 1998-11-05 IL IL12693098A patent/IL126930A0/xx unknown
- 1998-11-05 CZ CZ983587A patent/CZ358798A3/cs unknown
- 1998-11-05 BG BG102904A patent/BG102904A/xx unknown
- 1998-11-06 JP JP10330270A patent/JPH11228476A/ja active Pending
- 1998-11-09 ID IDP981467A patent/ID21253A/id unknown
- 1998-11-09 SK SK1543-98A patent/SK154398A3/sk unknown
- 1998-11-09 ES ES98309162T patent/ES2178812T3/es not_active Expired - Lifetime
- 1998-11-09 EP EP98309162A patent/EP0916640B1/de not_active Expired - Lifetime
- 1998-11-09 AT AT98309162T patent/ATE219042T1/de not_active IP Right Cessation
- 1998-11-09 DE DE69805935T patent/DE69805935T2/de not_active Expired - Fee Related
- 1998-11-10 KR KR1019980047946A patent/KR19990045151A/ko not_active Ceased
- 1998-11-10 CA CA002253324A patent/CA2253324A1/en not_active Abandoned
- 1998-11-10 PL PL98329634A patent/PL329634A1/xx unknown
- 1998-11-10 GE GEAP19984564A patent/GEP20012507B/en unknown
- 1998-11-10 CO CO98066121A patent/CO5040065A1/es unknown
- 1998-11-11 NO NO985261A patent/NO985261L/no not_active Application Discontinuation
- 1998-11-11 YU YU51198A patent/YU51198A/sh unknown
- 1998-11-11 TR TR1998/02286A patent/TR199802286A2/xx unknown
- 1998-11-11 HU HU9802620A patent/HUP9802620A1/hu unknown
- 1998-11-11 EA EA199800916A patent/EA001751B1/ru not_active IP Right Cessation
- 1998-11-11 ZA ZA9810321A patent/ZA9810321B/xx unknown
- 1998-11-11 SG SG1998004646A patent/SG73582A1/en unknown
- 1998-11-11 AR ARP980105702A patent/AR016677A1/es unknown
- 1998-11-11 NZ NZ332755A patent/NZ332755A/xx unknown
- 1998-11-11 AU AU92332/98A patent/AU745695B2/en not_active Ceased
- 1998-11-11 BR BR9804586-5A patent/BR9804586A/pt not_active IP Right Cessation
- 1998-11-12 CN CN98122455A patent/CN1131191C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EA199800916A1 (ru)	1999-08-26
CZ358798A3 (cs)	1999-06-16
AR016677A1 (es)	2001-07-25
ID21253A (id)	1999-05-12
CA2253324A1 (en)	1999-05-12
ATE219042T1 (de)	2002-06-15
BR9804586A (pt)	2000-02-29
GEP20012507B (en)	2001-08-27
NO985261D0 (no)	1998-11-11
CN1222501A (zh)	1999-07-14
CO5040065A1 (es)	2001-05-29
HU9802620D0 (en)	1998-12-28
EA001751B1 (ru)	2001-08-27
DE69805935T2 (de)	2002-10-10
HUP9802620A1 (hu)	1999-12-28
AU9233298A (en)	1999-06-03
PL329634A1 (en)	1999-05-24
TR199802286A3 (tr)	1999-06-21
AU745695B2 (en)	2002-03-28
TW467889B (en)	2001-12-11
IL126930A0 (en)	1999-09-22
BG102904A (en)	1999-10-29
EP0916640A1 (de)	1999-05-19
NZ332755A (de)	2000-03-27
ZA9810321B (en)	2000-06-21
TR199802286A2 (xx)	1999-06-21
CN1131191C (zh)	2003-12-17
SG73582A1 (en)	2000-06-20
NO985261L (no)	1999-05-14
KR19990045151A (ko)	1999-06-25
EP0916640B1 (de)	2002-06-12
ES2178812T3 (es)	2003-01-01
JPH11228476A (ja)	1999-08-24
YU51198A (sh)	2001-07-10
DE69805935D1 (de)	2002-07-18

Publication	Publication Date	Title
US4263319A (en)	1981-04-21	4-Substituted-2-indanol insecticidal ester derivatives
GB2046732A (en)	1980-11-19	Halogenated cyclopropane carboxylic acid esters
US4339457A (en)	1982-07-13	3-(Pyrrol-1-yl)phenylmethyl esters and intermediates
CZ295292B6 (cs)	2005-06-15	l,4-Diaryl-2-fluor-2-butenová insekticidní a akaricidní činidla, způsob jejich přípravy, kompozice obsahující tato činidla a způsob kontroly hmyzu a škodlivých roztočů
US5998673A (en)	1999-12-07	1, 4-diaryl-2-fluoro-2-butene insecticidal and acaricidal agents
US5849958A (en)	1998-12-15	1,4,diaryl-2-fluoro-2-butene insecticidal and acaricidal agents
JPS623146B2 (de)	1987-01-23
SK154398A3 (en)	1999-07-12	1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents
US6288011B1 (en)	2001-09-11	1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents
US5710102A (en)	1998-01-20	Difluorovinylsilane insecticidal and acaricidal agents
US4346251A (en)	1982-08-24	4-Substituted-2-indanols
HK1019583A (en)	2000-02-18	1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents
US6506800B2 (en)	2003-01-14	1,4 diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents
HK1002860A (en)	1998-09-25	1,4-diaryl-2-fluoro-2-butene insecticidal and acaricidal agents
EP0796860A2 (de)	1997-09-24	Difluorvinylsilane als insektizide und akarizide Mittel
MXPA97003924A (en)	1998-11-16	Insecticides and accaricides of 1,4-diaril-2-fluoro-2- but
GB2093831A (en)	1982-09-08	4-substituted-2-indanols and insecticidal ester derivatives