DE2941332C2 - - Google Patents

Info

Publication number: DE2941332C2
Authority: DE; Germany
Prior art keywords: general formula; compounds; active ingredient; compound; weight
Prior art date: 1978-10-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

DE2941332A

Other languages

German (de)

English (en)

Other versions

DE2941332A1 (de

Inventor

Michael John Lower Halstow Kent Gb Bull

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

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.)

1978-10-13

Filing date

1979-10-11

Publication date

1988-10-06

1979-10-11 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1980-04-30 Publication of DE2941332A1 publication Critical patent/DE2941332A1/de

1988-10-06 Application granted granted Critical

1988-10-06 Publication of DE2941332C2 publication Critical patent/DE2941332C2/de

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 28
-1 2-bromobenzyl ester Chemical class 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000575 pesticide Substances 0.000 claims description 5
239000004094 surface-active agent Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
241000255925 Diptera Species 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
241000256250 Spodoptera littoralis Species 0.000 description 5
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
241001425390 Aphis fabae Species 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000238876 Acari Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
230000000977 initiatory effect Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000012085 test solution Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
AHZWBOMWAKYLIS-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1CBr AHZWBOMWAKYLIS-UHFFFAOYSA-N 0.000 description 2
241000239290 Araneae Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
241000131102 Oryzaephilus Species 0.000 description 2
241000238680 Rhipicephalus microplus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000015278 beef Nutrition 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
QUWIUNGLBXHRLM-TVQRCGJNSA-N (2-bromo-6-chlorophenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(=O)OCc1c(Cl)cccc1Br QUWIUNGLBXHRLM-TVQRCGJNSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
DMARBQGIQKLIPM-UHFFFAOYSA-N 1-bromo-3-chloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Br DMARBQGIQKLIPM-UHFFFAOYSA-N 0.000 description 1
IDVSZKGRCBMUQW-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C(Cl)Cl IDVSZKGRCBMUQW-UHFFFAOYSA-N 0.000 description 1
MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
240000001624 Espostoa lanata Species 0.000 description 1
235000009161 Espostoa lanata Nutrition 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
241000255967 Helicoverpa zea Species 0.000 description 1
241000238631 Hexapoda 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
239000005909 Kieselgur Substances 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
241000209149 Zea 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
210000001015 abdomen Anatomy 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
VVSMKOFFCAJOSC-UHFFFAOYSA-L disodium;dodecylbenzene;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 VVSMKOFFCAJOSC-UHFFFAOYSA-L 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds

Landscapes

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

DE19792941332 1978-10-13 1979-10-11 2-brombenzylester, ihre herstellung und ihre verwendung als schaedlingsbekaempfungsmittel Granted DE2941332A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7840420		1978-10-13

Publications (2)

Publication Number	Publication Date
DE2941332A1 DE2941332A1 (de)	1980-04-30
DE2941332C2 true DE2941332C2 (nl)	1988-10-06

Family

ID=10500306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19792941332 Granted DE2941332A1 (de)	1978-10-13	1979-10-11	2-brombenzylester, ihre herstellung und ihre verwendung als schaedlingsbekaempfungsmittel

Country Status (8)

Country	Link
BE (1)	BE879142A (nl)
CH (1)	CH643230A5 (nl)
DE (1)	DE2941332A1 (nl)
FR (1)	FR2438645A1 (nl)
GB (1)	GB2035301B (nl)
IT (1)	IT1124604B (nl)
LU (1)	LU81778A1 (nl)
NL (1)	NL7907497A (nl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3145448A1 (de) *	1980-11-18	1982-08-26	Kuraray Co., Ltd., Kurashiki, Okayama	Substitutierter bezylester einer 2,2-dimethyl-3-(2,2-dihalogenvinyl)cyclopropancarbonsaeure, diese enthaltende pestizide mittel sowie verfahren zur bekaempfung von schaedlingen
DE3671428D1 (de) *	1985-12-10	1990-06-28	Roussel Uclaf	Jodsubstituierte cyclopropancarbonsaeurederivate, ihre herstellung, ihre verwendung als parasitizide fuer pflanzen und tiere und sie enthaltende zusammensetzungen.
FR2601360B2 (fr) *	1986-07-09	1988-11-10	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique a substituant iode, leur preparation, leur application a la lutte contre les parasites des vegetaux et des animaux.
FR2591223B1 (fr) *	1985-12-10	1988-03-18	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique a substituant iode, leur preparation, leur application a la lutte contre les parasites des vegetaux et des animaux
FR2641275B1 (fr) *	1988-12-29	1991-10-11	Roussel Uclaf	Nouveaux derives fluores de l'acide 3-ethenyl 2,2-dimethyl cyclopropane carboxylique, leur procede de preparation et leur application comme pesticides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE786808A (fr) *	1971-07-28	1973-01-29	Johnson & Son Inc S C	Chrysanthemumates de benzyle
GB1533854A (en) *	1975-03-11	1978-11-29	Shell Int Research	Benzyl thioamides and their use as pesticides
DE2658074C2 (de) *	1976-12-22	1986-12-04	Bayer Ag, 5090 Leverkusen	Cyclopropancarbonsäureester von halogenierten Benzylalkoholen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten und Akariden
US4183950A (en) *	1976-12-22	1980-01-15	Bayer Aktiengesellschaft	Combating arthropods with 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid esters of halogenated benzyl alcohols

1979
- 1979-09-17 GB GB7932152A patent/GB2035301B/en not_active Expired
- 1979-10-02 BE BE1/9548A patent/BE879142A/nl not_active IP Right Cessation
- 1979-10-10 NL NL7907497A patent/NL7907497A/nl not_active Application Discontinuation
- 1979-10-11 CH CH915679A patent/CH643230A5/de not_active IP Right Cessation
- 1979-10-11 IT IT26436/79A patent/IT1124604B/it active
- 1979-10-11 LU LU81778A patent/LU81778A1/fr unknown
- 1979-10-11 FR FR7925325A patent/FR2438645A1/fr active Granted
- 1979-10-11 DE DE19792941332 patent/DE2941332A1/de active Granted

Also Published As

Publication number	Publication date
FR2438645A1 (fr)	1980-05-09
FR2438645B1 (nl)	1981-08-14
NL7907497A (nl)	1980-04-15
GB2035301B (en)	1982-12-08
CH643230A5 (de)	1984-05-30
BE879142A (nl)	1980-04-02
IT1124604B (it)	1986-05-07
IT7926436A0 (it)	1979-10-11
DE2941332A1 (de)	1980-04-30
LU81778A1 (fr)	1980-05-07
GB2035301A (en)	1980-06-18

Legal Events

Date	Code	Title
1986-11-06	8110	Request for examination paragraph 44
1988-10-06	D2	Grant after examination
1989-04-06	8364	No opposition during term of opposition
1995-10-05	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
CH630778A5 (de)	1982-07-15	Schaedlingsbekaempfungsmittel enthaltend einen substituierten benzylaether oder -thioaether.
DE2407024A1 (de)	1974-08-29	Zur schaedlingsbekaempfung geeignete cyclopropanderivate und verfahren zu ihrer herstellung
CH624831A5 (nl)	1981-08-31
DE2014879B2 (de)	1974-05-09	Diphenylmethanderivate und ihre Verwendung als Synergisten in insekticiden Mitteln
DE2941332C2 (nl)	1988-10-06
DE1667979C3 (de)	1978-06-01	13-Benzodioxolcarbamate sowie Verfahren zu deren Herstellung und Schädlingsbekämpfungsmittel mit einem Gehalt dieser Verbindungen
EP0276196B1 (de)	1991-09-18	Substituierte Dioxolanderivate
DE2422977C2 (de)	1984-01-12	Cyclopropan-carbonsäure-&alpha;-cyanbenzylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pestizide Mittel
DE2054512A1 (de)	1971-05-19	Pyranverbindungen, Verfahren zu ih rer Herstellung und ihre Verwendung als Pflanzenschutzmittel
DE2553991A1 (de)	1976-06-16	Spiro-cyclopropanderivate, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
DE2941312C2 (nl)	1989-01-26
DE2447735A1 (de)	1975-08-21	Spiro-cyclopropane, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
DE1443933C2 (de)	1972-07-13	Thiocyano-phenyl-isothiocyanate und ihre Verwendung als Schädlingsbekämpfungsmittel
EP0136451A2 (de)	1985-04-10	Arylmethylätherderivate, Schädlingsbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
DD215002A5 (de)	1984-10-31	Pestizide zusammensetzung
EP0145662A2 (de)	1985-06-19	Isothioharnstoffe
EP0098800A1 (de)	1984-01-18	Carbaminsäureester
DE2624530C2 (de)	1986-09-11	Sulfoniumsalze von 2-Nitro-2-(tetrahydro-2H-1,3-thiazin-2-yliden)-essigsäure-estern, Verfahren zu ihrer Herstellung und diese enthaltende insektizide Mittel
CH629082A5 (de)	1982-04-15	Schaedlingsbekaempfungsmittel enthaltend neue dispirocyclopropancarbonsaeureester als wirkstoffkomponente.
CH597753A5 (en)	1978-04-14	Aralkyl 2,2-dihalo-cyclopropane 3-carboxylates insecticides
DE2059424C3 (de)	1982-06-09	Verfahren zur Herstellung der β-Form von 1-Phenylvinylthiophosphonsäureester
CH642048A5 (de)	1984-03-30	Pentachlorbenzylester-derivate.
DD215001A5 (de)	1984-10-31	Pestizide zusammensetzung
DE3832656A1 (de)	1989-04-13	Substituierte carbamate
DE2813552A1 (de)	1978-10-05	Cyclopropylcarboxylate