LU85762A1 - Rodenticides a base de derives de la phenylpropargylamine - Google Patents

Rodenticides a base de derives de la phenylpropargylamine Download PDF

Info

Publication number: LU85762A1
Authority: LU; Luxembourg
Prior art keywords: group; compound; acid; carbon atoms; salts
Prior art date: 1984-02-08

Application number

LU85762A

Other languages

English (en)

French (fr)

Inventor

Leslie Roy Hatton

Original Assignee

May & Baker Ltd

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.)

1984-02-08

Filing date

1985-02-06

Publication date

1986-09-02

1984-02-08 Priority claimed from GB848403362A external-priority patent/GB8403362D0/en

1984-12-12 Priority claimed from GB848431375A external-priority patent/GB8431375D0/en

1985-02-06 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1986-09-02 Publication of LU85762A1 publication Critical patent/LU85762A1/fr

Links

IZKIWEYIOKPHLF-UHFFFAOYSA-N n-prop-2-ynylaniline Chemical class C#CCNC1=CC=CC=C1 IZKIWEYIOKPHLF-UHFFFAOYSA-N 0.000 title claims description 21
239000003128 rodenticide Substances 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims description 134
150000003839 salts Chemical class 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 53
-1 phenoxymethyl group Chemical group 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 46
238000000034 method Methods 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 34
241000283984 Rodentia Species 0.000 claims description 30
239000007787 solid Substances 0.000 claims description 30
239000007788 liquid Substances 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
241001465754 Metazoa Species 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 21
239000012141 concentrate Substances 0.000 claims description 18
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
241000607479 Yersinia pestis Species 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
241000699670 Mus sp. Species 0.000 claims description 10
241000700159 Rattus Species 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000005042 acyloxymethyl group Chemical group 0.000 claims description 8
125000004849 alkoxymethyl group Chemical group 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
239000003146 anticoagulant agent Substances 0.000 claims description 7
229940127219 anticoagulant drug Drugs 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
239000000969 carrier Substances 0.000 claims description 7
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 6
230000037406 food intake Effects 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
238000010348 incorporation Methods 0.000 claims description 5
239000008247 solid mixture Substances 0.000 claims description 5
239000013598 vector Substances 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
WFFZGYRTVIPBFN-UHFFFAOYSA-N 3h-indene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
235000001671 coumarin Nutrition 0.000 claims description 3
229960000956 coumarin Drugs 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
230000001119 rodenticidal effect Effects 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
231100000518 lethal Toxicity 0.000 claims 1
230000001665 lethal effect Effects 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical class NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims 1
239000011701 zinc Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 38
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
235000008504 concentrate Nutrition 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000003756 stirring Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
235000013312 flour Nutrition 0.000 description 8
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 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
235000013339 cereals Nutrition 0.000 description 6
239000013078 crystal Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
231100000636 lethal dose Toxicity 0.000 description 6
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239000002244 precipitate Substances 0.000 description 6
231100000331 toxic Toxicity 0.000 description 6
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000003085 diluting agent Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
235000013311 vegetables Nutrition 0.000 description 5
LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000010775 animal oil Substances 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
235000019219 chocolate Nutrition 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
235000005687 corn oil Nutrition 0.000 description 4
239000002285 corn oil Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000008158 vegetable oil Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
235000019483 Peanut oil Nutrition 0.000 description 3
208000005374 Poisoning Diseases 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
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235000013305 food Nutrition 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
235000014666 liquid concentrate Nutrition 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000000312 peanut oil Substances 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
239000002574 poison Substances 0.000 description 3
231100000614 poison Toxicity 0.000 description 3
231100000572 poisoning Toxicity 0.000 description 3
230000000607 poisoning effect Effects 0.000 description 3
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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244000075850 Avena orientalis Species 0.000 description 2
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COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
241000699660 Mus musculus Species 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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235000021307 Triticum Nutrition 0.000 description 2
DEXKHGVSCDMMLD-UHFFFAOYSA-N [ClH]1N=CC=C1 Chemical compound [ClH]1N=CC=C1 DEXKHGVSCDMMLD-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
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PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
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YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
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229910052757 nitrogen Inorganic materials 0.000 description 2
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COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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229930006000 Sucrose Natural products 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
235000015895 biscuits Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000009429 distress Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
230000009545 invasion Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000000123 paper Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000004033 plastic Substances 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000036280 sedation Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom

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)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

LU85762A 1984-02-08 1985-02-06 Rodenticides a base de derives de la phenylpropargylamine LU85762A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB848403362A GB8403362D0 (en)	1984-02-08	1984-02-08	Compositions of matter
GB8403362		1984-02-08
GB848431375A GB8431375D0 (en)	1984-12-12	1984-12-12	Compositions of matter
GB8431375		1984-12-12

Publications (1)

Publication Number	Publication Date
LU85762A1 true LU85762A1 (fr)	1986-09-02

Family

ID=26287301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU85762A LU85762A1 (fr)	1984-02-08	1985-02-06	Rodenticides a base de derives de la phenylpropargylamine

Country Status (15)

Country	Link
US (1)	US4871748A (da)
AU (1)	AU588795B2 (da)
BE (1)	BE901681A (da)
BR (1)	BR8500554A (da)
CA (1)	CA1280420C (da)
CH (1)	CH665836A5 (da)
DD (1)	DD235554A5 (da)
DE (1)	DE3504412A1 (da)
DK (1)	DK54085A (da)
FR (1)	FR2559149B1 (da)
GB (1)	GB2153827B (da)
IL (1)	IL74231A (da)
IT (1)	IT1183330B (da)
LU (1)	LU85762A1 (da)
NL (1)	NL8500347A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5252586A (en) *	1990-09-28	1993-10-12	The Du Pont Merck Pharmaceutical Company	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
ES2154570B1 (es) *	1998-10-23	2001-10-16	Almirall Prodesfarma Sa	Nuevos compuestos de peperidina y su uso como raticidas.
ATE327673T1 (de) *	2001-08-23	2006-06-15	Bayer Cropscience Sa	Substituierte propargylamine

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1483709A (fr) *	1962-07-11	1967-06-09		Composés basiques se rattachant au butane et leur préparation
GB1055548A (en) *	1965-08-23	1967-01-18	Acraf	New substituted 1-aryl-3-aminopropynes and process for their preparation
US4180574A (en) *	1978-12-26	1979-12-25	Abbott Laboratories	Certain ovicidal piperazines
US4285957A (en) *	1979-04-10	1981-08-25	Richardson-Merrell Inc.	1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof
ZA813127B (en) *	1980-05-13	1982-05-26	May & Baker Ltd	A new phenylpropargylamine derivative
US4634699A (en) *	1983-11-30	1987-01-06	Burroughs Wellcome Co.	Branched chain phenothiazine

1985
- 1985-01-23 US US06/693,729 patent/US4871748A/en not_active Expired - Fee Related
- 1985-01-31 FR FR8501530A patent/FR2559149B1/fr not_active Expired
- 1985-02-03 IL IL74231A patent/IL74231A/xx unknown
- 1985-02-06 CA CA000473676A patent/CA1280420C/en not_active Expired - Fee Related
- 1985-02-06 AU AU38487/85A patent/AU588795B2/en not_active Ceased
- 1985-02-06 LU LU85762A patent/LU85762A1/fr unknown
- 1985-02-06 DK DK54085A patent/DK54085A/da not_active Application Discontinuation
- 1985-02-07 BE BE0/214473A patent/BE901681A/fr not_active IP Right Cessation
- 1985-02-07 BR BR8500554A patent/BR8500554A/pt unknown
- 1985-02-07 CH CH562/85A patent/CH665836A5/fr not_active IP Right Cessation
- 1985-02-07 NL NL8500347A patent/NL8500347A/nl not_active Application Discontinuation
- 1985-02-07 GB GB08503123A patent/GB2153827B/en not_active Expired
- 1985-02-08 DD DD85273149A patent/DD235554A5/de unknown
- 1985-02-08 DE DE19853504412 patent/DE3504412A1/de not_active Withdrawn
- 1985-02-08 IT IT19442/85A patent/IT1183330B/it active

Also Published As

Publication number	Publication date
CA1280420C (en)	1991-02-19
AU588795B2 (en)	1989-09-28
DD235554A5 (de)	1986-05-14
IT1183330B (it)	1987-10-22
IL74231A (en)	1988-10-31
GB8503123D0 (en)	1985-03-13
BE901681A (fr)	1985-08-07
GB2153827A (en)	1985-08-29
BR8500554A (pt)	1985-09-24
DE3504412A1 (de)	1985-08-08
CH665836A5 (fr)	1988-06-15
US4871748A (en)	1989-10-03
GB2153827B (en)	1987-10-21
FR2559149B1 (fr)	1989-11-24
IT8519442A0 (it)	1985-02-08
AU3848785A (en)	1985-08-15
IL74231A0 (en)	1985-05-31
DK54085A (da)	1985-08-09
FR2559149A1 (fr)	1985-08-09
DK54085D0 (da)	1985-02-06
NL8500347A (nl)	1985-09-02

Publication	Publication Date	Title
CH638787A5 (fr)	1983-10-14	Esters d'acides 4-(4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy)-2-pentenoiques utiles comme herbicides.
MC1756A1 (fr)	1987-04-24	Composes pesticides,procede pour les preparer,compositions et melange les contenant,procede de lutte contre les nuisibles les utilisant et leur utilisation en medecine
FR2586416A1 (fr)	1987-02-27	Nouvelles 2-(1-(3-chlorallyloxyamino)alkylidene)-5-alkylthioalkyl-cyclohexane-1,3-diones, composition herbicide les contenant, leur procede de preparation et leurs applications
LU85762A1 (fr)	1986-09-02	Rodenticides a base de derives de la phenylpropargylamine
EP0105006B1 (fr)	1986-03-19	Cyclopropane carboxylates à structure allénique, leur procédé et leurs intermédiaires de préparation, leur application à la lutte contre les parasites et les compositions les renfermant
KR840002065B1 (ko)	1984-11-09	페닐프로파르길아민 유도체의 제조방법
CH660179A5 (fr)	1987-03-31	Derives de 1-phenoxy(phenylthio)-4-arylalkynyloxy-benzene pourvus d'une activite acaricide et d'une activite hormonale juvenile.
FR2472340A1 (fr)	1981-07-03	Attractant composite d'insectes, pour les agrotis males a ligne blanche et procede de preparation des constituants actifs de cet attractant
MC1767A1 (fr)	1987-07-17	Composes pesticides,procedes pour leur preparation et composition insecticide ou acaricide,composition pesticide synergisee et melange en contenant
BE574921A (da)
BE897560A (fr)	1984-02-20	Derives herbicides de 5-desoxy-3-0-arylmethyl- ou (aryl substitue) methyl-1,2-0-alcoylidene-a-d xylofurannoses
CH640836A5 (fr)	1984-01-31	1-(2,6-dihalobenzoyl)-3-(2-pyridinyl-5-substitue)urees, leur preparation, et composition insecticide les contenant.
CH640698A5 (fr)	1984-01-31	Composition herbicide.
BE826376A (fr)	1975-09-08	Dinitroanilines
AT388916B (de)	1989-09-25	Verfahren zur herstellung von neuen phenylpropargylaminderivaten und deren saeureadditionssalzen
FR2512023A1 (fr)	1983-03-04	5-phenoxyphenyltetrahydro-1,3,5-thiadiazine-4-ones, leur preparation et leur utilisation dans la lutte contre les parasites
CH618843A5 (da)	1980-08-29
CH629796A5 (en)	1982-05-14	Therapeutically active compounds of 4-(2-thienylmethylamino)benzoic acid
CA2788441A1 (fr)	2011-08-25	Composes rodenticides, composition les comprenant et leur utilisation pour lutter contre les rongeurs nuisibles
BE796753A (fr)	1973-09-14	Nouveaux phenyl-carbamates de pyridyle doues d'activite rodenticide et composition les contenant
JPS58113107A (ja)	1983-07-05	除草剤
BE880478A (fr)	1980-06-06	Benzimidazole-carbamates
FR2458999A1 (fr)	1981-01-09	Nouvelles compositions herbicides non phytotoxiques a l'egard des recoltes
BE737232A (en)	1970-01-16	1,1-dichloroalkene-1 derivatives
BE624872A (da)