Crystalline modification of fipronil

Patent metadata

Field	Value
Publication number	US-9451772-B2
Application number	US-201313746868-A
Country	US
Kind code	B2
Filing date	Jan 22, 2013
Priority date	Nov 10, 2006
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

The present invention relates to a novel crystalline modification of fipronil, to a process for the preparation of the same, to pesticidal and parasiticidal mixtures and compositions comprising said crystalline modification and to their use for combating pests and parasites.

First claim

The invention claimed is:

1. A synergistic pesticidal or parasiticidal mixture comprising, as active components, a solid fipronil comprising at least 85% by weight of crystalline modification I fipronil being present in the monoclinic system having the centrosymmetric space group C2/c and showing, in an X-ray powder diffractogram at 25° C., at least 7 of the following reflexes:
d= 7.45±0.1 Å  (1)

d= 6.07±0.07 Å  (2)

d= 5.57±0.05 Å  (3)

d= 4.84±0.05 Å  (4)

d= 3.76±0.05 Å  (5)

d= 3.67±0.05 Å  (6)

d= 3.23±0.05 Å  (7)

d= 3.01±0.05 Å  (8)

d= 2.77±0.05 Å  (9)

and one or more pesticidal or parasiticidal compounds selected from the group consisting of:
A.3. bifenthrin and alpha-cypermethrin
A.5. a nicotinic receptor agonist/antagonist compound selected from: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid;
the thiazol compound of formula Γ 1

A.7. a macrocyclic lactone insecticide selected from: abamectin and emamectin;
A.15. anthranilamide compounds of formula Γ 3

wherein A 1 is CH 3 , Cl, Br, I, X is C—H, C—Cl, C—F or N, Y′ is F, Cl, or Br, Y″ is hydrogen, F, Cl, CF 3 , B 1 is hydrogen, Cl, Br, I, CN, B 2 is Cl, Br, CF 3 , OCH 2 CF 3 , OCF 2 H, and R B is hydrogen, CH 3 or CH(CH 3 ) 2 ;
a fungicidal compound IIA selected from the list comprising strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxy-imino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxy-imino)ethyl]benzyl)carbamate, and methyl 2-(ortho-((2,5-dimethylphenyloxy-methylene)phenyl)-3-methoxyacrylate;
wherein fipronil and the one or more pesticidal or parasiticidal compounds are present in a ratio of 500:1 to 1:100.

2. The mixture of claim 1 , wherein one or more pesticidal or parasiticidal compounds is pyraclostrobin.

3. The mixture of claim 1 , further comprising compound IIB selected from the group consisting of captan, carbendazim, dodemorph, epoxiconazole, fenbuconazole, fenoxanil, fenpropimorph, fludioxonil, flutriafol, imazalil, iprodione, metalaxyl, probenazol, prothioconazole, pyrimethanil, thiophanate-methyl, triadimenol, ziram, boscalid, trifloxystrobin, chlorothalonil, cyproconazole, ethaboxam, fluquinconazole, guazatin, hymexazole, ipconazole, mancozeb, metconazole, metiram, aldimorph, orysastrobin, propiconazole, pyraclostrobin, thiabendazole, thiram, triticonazole, metrafenone, tebuconazole, and triticonazole.

4. A method for controlling pests which comprises contacting the pests or their food supply, habitat, breeding grounds or their locus with a pesticidally effective amount of the mixture of claim 1 .

5. The method of claim 4 , wherein the one or more pesticidal or parasiticidal compounds is pyraclostrobin.

6. The method of claim 4 , wherein the mixture further comprises compound IIB selected from the group consisting of captan, carbendazim, dodemorph, epoxiconazole, fenbuconazole, fenoxanil, fenpropimorph, fludioxonil, flutriafol, imazalil, iprodione, metalaxyl, probenazol, prothioconazole, pyrimethanil, thiophanate-methyl, triadimenol, ziram, boscalid, trifloxystrobin, chlorothalonil, cyproconazole, ethaboxam, fluquinconazole, guazatin, hymexazole, ipconazole, mancozeb, metconazole, metiram, aldimorph, orysastrobin, propiconazole, pyraclostrobin, thiabendazole, thiram, triticonazole, metrafenone, tebuconazole, and triticonazole.

7. A method for protecting a plant from infestation and attack by pests, which comprises applying to the foliage or stem of said plant a pesticidally effective amount of the mixture of claim 1 .

8. The method of claim 7 , wherein the one or more pesticidal or parasiticidal compounds is pyraclostrobin.

9. The method of claim 7 , wherein the mixture further comprises compound IIB selected from the group consisting of captan, carbendazim, dodemorph, epoxiconazole, fenbuconazole, fenoxanil, fenpropimorph, fludioxonil, flutriafol, imazalil, iprodione, metalaxyl, probenazol, prothioconazole, pyrimethanil, thiophanate-methyl, triadimenol, ziram, boscalid, trifloxystrobin, chlorothalonil, cyproconazole, ethaboxam, fluquinconazole, guazatin, hymexazole, ipconazole, mancozeb, metconazole, metiram, aldimorph, orysastrobin, propiconazole, pyraclostrobin, thiabendazole, thiram, triticonazole, metrafenone, tebuconazole, and triticonazole.

10. The method of claim 7 , wherein the solid fipronil is applied in an amount of from 5 g/ha to 2000 g/ha.

11. The method of claim 10 , wherein the one or more pesticidal or parasiticidal compounds is pyraclostrobin.

12. The method of claim 10 , wherein the mixture further comprises compound IIB selected from the group consisting of captan, carbendazim, dodemorph, epoxiconazole, fenbuconazole, fenoxanil, fenpropimorph, fludioxonil, flutriafol, imazalil, iprodione, metalaxyl, probenazol, prothioconazole, pyrimethanil, thiophanate-methyl, triadimenol, ziram, boscalid, trifloxystrobin, chlorothalonil, cyproconazole, ethaboxam, fluquinconazole, guazatin, hymexazole, ipconazole, mancozeb, metconazole, metiram, aldimorph, orysastrobin, propiconazole, pyraclostrobin, thiabendazole, thiram, triticonazole, metrafenone, tebuconazole, andtriticonazole.

13. A method for protecting seed comprising contacting the seeds with the mixture of claim 1 in pesticidally effective amounts.

14. The method of claim 13 , wherein the mixture is applied in an amount of from 0.1 g to 10 kg per 100 kg of seeds.

15. The method of claim 14 , wherein the one or more pesticidal or parasiticidal compounds is pyraclostrobin.

16. The method of claim 14 , wherein the mixture further comprises compound IIB selected from the group consisting of captan, carbendazim, dodemorph, epoxiconazole, fenbuconazole, fenoxanil, fenpropimorph, fludioxonil, flutriafol, imazalil, iprodione, metalaxyl, probenazol, prothioconazole, pyrimethanil, thiophanate-methyl, triadimenol, ziram, boscalid, trifloxystrobin, chlorothalonil, cyproconazole, ethaboxam, fluquinconazole, guazatin, hymexazole, ipconazole, mancozeb, metconazole, metiram, aldimorph, orysastrobin, propiconazole, pyraclostrobin, thiabendazole, thiram, triticonazole, metrafenone, tebuconazole, and triticonazole.

17. A seed treated with the mixture of claim 1 in an amount of from 0.1 g to 10 kg per 100 kg of seeds.

18. A method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of the mixture of claim 1 .

19. The mixture of claim 1 , wherein the one or more pesticidal or parasiticidal compound is selected from the reduced group A.3 being bifenthrin and alpha-cypermethrin.

20. The mixture of claim 1 , wherein the one or more pesticidal or parasiticidal compound is selected from the group A.5.

21. The mixture of claim 1 , wherein the one or more pesticidal or parasiticidal compound is selected from the group A.7.

22. The mixture of claim 1 , wherein the one or more pesticidal or parasiticidal compound is an anthranilamide compound of formula Γ 3 wherein A 1 is C

Assignees

• Basf Se

Inventors

• Saxell Heidi Emilia
• Erk Peter
• Taranta Claude
• Kroehl Thomas
• Cox Gerhard
• Sukopp Martin
• Scherer Stefan
• Ojala Antti
• Desiraju Gautam R
• Banerjee Rahul
• Bhatt Prashant M

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/10

  Anthelmintics · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N47/02 Primary

  the carbon atom having no bond to a nitrogen atom · CPC title