CA1284638C - DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES - Google Patents

DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES

Info

Publication number: CA1284638C
Authority: CA; Canada
Prior art keywords: beta; milbemycin; tert; butyldimethylsilyl; formula
Prior art date: 1987-06-29
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 - Lifetime

Application number

CA000540797A

Other languages

English (en)

Inventor

Anthony Cornelius O'sullivan

Bruno Frei

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.)

Ciba Geigy Investments Ltd

Original Assignee

Ciba Geigy AG

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.)

1987-06-29

Filing date

1987-06-29

Publication date

1991-06-04

1987-06-29 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1987-06-29 Priority to CA000540797A priority Critical patent/CA1284638C/fr

1991-06-04 Application granted granted Critical

1991-06-04 Publication of CA1284638C publication Critical patent/CA1284638C/fr

2008-06-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000575 pesticide Substances 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 104
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 72
239000001257 hydrogen Substances 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 25
241000607479 Yersinia pestis Species 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract 2
-1 cycloaliphatic Chemical group 0.000 claims description 65
239000013543 active substance Substances 0.000 claims description 31
239000000460 chlorine Substances 0.000 claims description 27
125000001424 substituent group Chemical group 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 24
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
229910052801 chlorine Inorganic materials 0.000 claims description 20
235000017168 chlorine Nutrition 0.000 claims description 20
229940060038 chlorine Drugs 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 17
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
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150000002367 halogens Chemical group 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 11
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125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
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125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 6
244000045947 parasite Species 0.000 claims description 6
150000003566 thiocarboxylic acids Chemical class 0.000 claims description 6
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150000004820 halides Chemical class 0.000 claims description 4
230000003472 neutralizing effect Effects 0.000 claims description 4
150000002905 orthoesters Chemical class 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
238000009826 distribution Methods 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
230000006378 damage Effects 0.000 claims description 2
244000078703 ectoparasite Species 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
244000079386 endoparasite Species 0.000 claims 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
230000000361 pesticidal effect Effects 0.000 abstract description 2
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239000000203 mixture Substances 0.000 description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
238000005160 1H NMR spectroscopy Methods 0.000 description 23
239000000243 solution Substances 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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150000002431 hydrogen Chemical group 0.000 description 16
239000000741 silica gel Substances 0.000 description 14
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
239000012043 crude product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
241000238876 Acari Species 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
241001494479 Pecora Species 0.000 description 8
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 8
FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000005660 Abamectin Substances 0.000 description 6
241000244206 Nematoda Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
125000001153 fluoro group Chemical group F* 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
239000000969 carrier Substances 0.000 description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
235000013601 eggs Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
150000003556 thioamides Chemical class 0.000 description 5
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
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RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 3
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 3
230000037396 body weight Effects 0.000 description 3
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 3
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125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
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150000003904 phospholipids Chemical class 0.000 description 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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235000012424 soybean oil Nutrition 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
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239000008117 stearic acid Chemical class 0.000 description 1
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125000000542 sulfonic acid group Chemical group 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000540797A 1987-06-29 1987-06-29 DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES Expired - Lifetime CA1284638C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000540797A CA1284638C (fr)	1987-06-29	1987-06-29	DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000540797A CA1284638C (fr)	1987-06-29	1987-06-29	DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES

Publications (1)

Publication Number	Publication Date
CA1284638C true CA1284638C (fr)	1991-06-04

Family

ID=4135998

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000540797A Expired - Lifetime CA1284638C (fr)	1987-06-29	1987-06-29	DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES

Country Status (1)

Country	Link
CA (1)	CA1284638C (fr)

1987
- 1987-06-29 CA CA000540797A patent/CA1284638C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1998-06-04	MKLA	Lapsed

Publication	Publication Date	Title
US4859657A (en)	1989-08-22	Pesticides
CA1300609C (fr)	1992-05-12	13-spiro-2'-¬tetrahydrofurane\|-milbemycines, leur procede de preparation et leur utilistion contre les parasites et les insectes nuisibles
US4134973A (en)	1979-01-16	Carbohydrate derivatives of milbemycin and processes therefor
EP0008184B1 (fr)	1984-05-02	Dérivés alcoylés des composés C-076, leur préparation et leur emploi comme produits antiparasitaires
EP0040913B1 (fr)	1984-07-25	Dérivés des composés C-076, leur préparation et utilisation anti-parasitaire
AU596644B2 (en)	1990-05-10	C(29)-carbonyloxymilbemycin derivatives for controlling parasitic pests of animals and plants
US4806527A (en)	1989-02-21	Avermectin derivatives
GB2167751A (en)	1986-06-04	Pesticidal 13b-substituted milbemycin derivatives
GB1579118A (en)	1980-11-12	Carbohydrate derivatives of milbemycin
CA1261824A (fr)	1989-09-26	Pesticides
EP0102721B1 (fr)	1985-11-21	Dérivés de la milbemycine D, leur préparation et les compositions les contenant
US4582852A (en)	1986-04-15	14- and 15-hydroxy milbemycin derivatives for controlling plant and animal parasites
EP0189159A2 (fr)	1986-07-30	Dérivés de la 13-bêta-alkyl-milbémycine pour combattre les parasites affectant les animaux et les plantes
CA1254886A (fr)	1989-05-30	Lactoses, procede de preparation et utilisation dans la lutte contre les animaux nuisibles
CA1242436A (fr)	1988-09-27	Derive de lactone, sa preparation, et son emploi pour la repression des insectes
US4954484A (en)	1990-09-04	Parasiticides and insecticides
CA1284638C (fr)	1991-06-04	DERIVES DE LA 13.beta.-MILBEMYCINE ET LEUR UTILISATION COMME PESTICIDES
US4897416A (en)	1990-01-30	Insecticides and parasiticides
AU621593B2 (en)	1992-03-19	Insecticides and parasiticides
EP0340932B1 (fr)	1995-01-18	Agents antiparasitaires du type des avermectines
EP0253378A2 (fr)	1988-01-20	Dérivés des antibiotiques S541 substitués en position 13-bêta par un alkyle, pour combattre les parasites des animaux domestiques et des plantes
SI8810047A8 (en)	1995-12-31	13 beta miebemicyn's derivates,process for their preparation and use thereof as pesticides