AU8926898A

AU8926898A - Pesticidal composition

Info

Publication number: AU8926898A
Application number: AU89268/98A
Authority: AU
Inventors: Fernando Augusto Godoy; Claudio Toledo Netto; Sergio Zambon
Original assignee: Rhone Poulenc Agro SA; Rhone Poulenc Agrochimie SA
Current assignee: Bayer CropScience SA
Priority date: 1997-10-15
Filing date: 1998-10-14
Publication date: 1999-05-06
Anticipated expiration: 2018-10-14
Also published as: AR017519A1; AU757695B2; ES2155750A1; OA10900A; TR199802070A2; TR199802070A3; IL126549A; ZA989379B; BR9705278A; IL126549A0; AP1161A; ES2155750B1; MA24809A1; EG23068A; AP9801406A0

Description

II

i 11

AUSTRALIA

PATENTS ACT 1990 COMPLETE SPECIFICATION NAME OF APPLICANT(S): Rhone-Poulenc Agro ADDRESS FOR SERVICE: DAVIES COLLISON CAVE Patent Attorneys I Little Collins Street, Melbourne, 3000.

INVENTION TITLE: Pesticidal composition The following statement is a full description of this invention, including the best method of performing it known to me/us:it i 3r- ~i/i.

S- la lihe present invention relates to a new pesticidal composition and a method of Lsing the composition.

S The problem of ant control is a particularly ubiquitous one in most regions of the world. Either ants can be a nuisance by the invasion of buildings or attack of foodstuffs. or ants can destroy agricultural resources. Particularly the problem of ant control by the use of non-repellent baits is an acute one with respect to leaf-cutting ants.

It is also a problem to prepare pesticidal formulations that are increasingly environmentally innocuous. It is highly advantageous to distribute a pesticide in a form in which the formulation may serve as a proper dispersant and then disappear by substantially quick degradation.

It is an object of the present invention to provide a new formulation of a pesticide.

Another object of the present invention is to provide a substantially nonrepellent bait for ants, particularly leaf-cutting ants.

Another object of the present invention is to provide a formulation that is i favorable to the environment.

'0 These objects are met in whole or in part by the present invention.

The present invention provides a composition comprising a compound of formula R7 R N T' I S 'Is haoi dz i~Io aak IZ' R 4 is selected from thee group conSISting of hydrog-en, halogen. R -CM00 7 7 alk-l. liaioalk\ 1. -OR, -N=C1LR I tp and -C(OhalkvI: Rj and PR 6 Ire independently selected frOm Li h-,drogen atom., alk, 1, haioalk. 1.

~~alkvlene radical which may be interrupted by, one or more htraos I)prefi-rably selecte~d from11 OXeN. uII troiQen aId sulfUr;

R-

7 Is selected f'rOm alk' and haloalk-vl: R, is selected from alk L. hialoalkyl and liPIdroicii: Rq iS Selected ti-1 drogen rand ik-1:

R

1 Is selected from pho.nvl or hceroar% I each of wich is uinsubstituted or SubhStit(utedU one or more hivdrox-. balooen. -O-alkvl. -S-ilk-vl. cvano. ora:lkvl (,rI com1binations theretiC X Is selected from nitrogen and -C-RI-i

R

1 I and Rp are independentIN selected f'ront halogten or hydrogen or CN or NO-: R; isselected from hialogen. haloalkyL haboalkoxy. -S O)qC S: -1In. n. q. r are independently selected from 0- 1. and..2: Provided that when R I IS methyl. R- is haloalkyl. R 4 is R 1 is Cl1. RI 3 is CF-,.

and X is N and provided that w,%hen R, is 4.5-dic-vanoimidazol 2-yt. R 4 Is Cl.- R I is Cl. R 1 3 is and X is =C-Cl and a fruit component- The alkvl and aLiKoxy groups and moieties thereof of the formula (11l are preferably lower alkyl and aikox rus that. is. groups havingc one to six carbon atoms. The haloalkvl and haloalkoxy rop likewise preferably have one to four carbon atoms. The haloalkvI and haloalkoxv g-roup~s can bear one or more halogen U2 ~D I'ccrc IPtS 01'11hi. t'Xfpe includ-e -C F- and -DCF. It shall be ilhai tI 11L n iorj thle d' aictit 'W1K kkne radical represented b% R- an an !tncludinc_ the nitro atomi to xvhich R.s and R6 are attached is gzenerall% a 5- 6. or 7 niembered ring. When Rjo is heteroaryl. it is preferably pyridyl, most preferably 2- :'pyridyl. It wvill be understood that the Il-arylpyrazoles of fornula include enantioners andlor diastereomlers thereof.

Compounds of formula may be prepared according to known processes, for example ais described in International Patent Publications WO 8713781. 93i6089, and 94.-2- 1606 as -well as in European Patent Applications 2.95 117. 403300. 385809 or 679650. German Patent Publication 19511269 and United States Patents 5232940 and 5236938 or other process accordimng to the knowled-e of a man skilled in th art o chemnical svnthesis, which is deemed to include the Chemical Abstract and the literature refer-red to therein.

the compound of formula has one or mor e of the followinit features wherein: R IIs CN:

R

4 is -NR-R 6 R_ and PR 6 are independently selected from the hydrogen 0 atom. alkyl. haloalkvi C(O)alkvl. C(O)0R 7 X is C-R12- or R 1 3 is selected from a halogen atom. haloalkyvl. haloalkoxy.

and -SF 5 A preferable. group of compounds of the composition is that wherein: 2I Ris CN:

R

3 is a haloalkyl radical: R4. is NH-) X is C-RI 1

RI

1 and R 1 2 represent, indepenidently of one another, a halogen atom: and -4- R 3 is a haloalkyl radical.

Most prctleraly the compound of Iformula u the composilion is -aninO-3cvano-I-( 2.0-dichloro-4-tri luoronicthylphcniyl)-4-tri ILIoroIntethylnS lpy Ipxrazole.

hereafter designated as Compound The composition generally comprises from about 0.1 g to 1000 g of the compound of formula per metric ton of the total composition, preferably I g to 200 Sg per metric ton, more preferably from 1 to lOOg per metric ton, even more preferably from 10 to 100g per metric ton, most preferably from 20 to 50 g per metric ton. In other words, the range of the ratio of the compound of formula to the total composition is from about 10' :1 to about 10-' preferably from 1 to about 2x10': 1, preferably from about 10': 1 to about 10': 1, and most preferaliy from about 10": 1 to about 10: 1.

The fruit component is preferably an orange component. The orange component of the composition generally comprises the parts of the orange after the juice has been substantially removed, that is to say after the orange has been substantially squeezed; or in other words, a bagasse of orange. Generally the removal ofjuice is in a juicing process employed in commercial production of orange juice.

The orange component of the invention generally comprises the skin and pulp of the S•orange. It. preferably comprises the dried residue of the orange or an orange that is substantially dried.

It has been found that the most preferred fruit component that may be used in he present invention is that which is substantially free of aninsecticide other than that of formula Preferably, the fruit component is substantially free ofa pyrethrin or a ".pyrethroid insecticide. By the term substantially free is meant fruit components which have a level of insecticide or insecticide residue which is generally undetectable by S" ants. Preferably, the insecticide constitutes by weight from 1 part per billion (ppb) to parts per million (ppm). preferably from 2 ppb to 1000 ppb, more preferably from ppb to 100 ppb. By the term ppb is meant parts per 1,000,000,000, or in other words, the term as defined in the United States of America.

Most preferably, the fruit from which the fruit component is obtained are grown using no pesticide, that is generally no insecticide, herbicide, or fungicide. Ifa :pesticide is used, then it is preferred that there be a lengthy pre-harvest interval (PHI) from the time of the last pesticide application until harvest. Preferably the PHI is i: ti m 1-4 months. pretcrabi from i 0to months and ,most preferabl from I to months..

ihe amount of the fruit component is as a eight percentae of the total conposition is from about 50", to about preferably from about 60% to about S So most preferably from about 80% to about The composition also comprises anaggregant, preferably an oil. preferably a vueetable oil. A vegetable oil is that which is derived from plants. Vegetable oils that nmav be utilized in the composition include soybean oil. corn oil. rapeseed oil (or canola oil) and peanut oil. The weightiweight percentage of the oil is from about 0.01% to about 30%. preferably from 0.5% to about 30%. more preferably from about 1% to about 15%. even more preferably from about 1% to about 10%. most preferably from 1% to The composition of the presen invention optionally comprises a starch comoonent- The starch component generally is a farinaceous product which including a ground corn product. wheat bran. cotton bran. rice bran. peanut, soy. rye. or other cereals. or mixtures thereof. Preferably the starch component is a ground corn S: ,product.

S oGround corn products that may be used according to the present invention Sinclude: cornmeal. corn flour, grits (also known as ground hominy corn without germ). creme de milho twhich translated from Brazilian Portuguese generally means creme of corn); fub. (which translated from Brazilian Portuguese generally includes cornmeal andlor cornflour).

l 'Generally the amount of the starch component is from 0.01% to 40% by g weight of the total composition. preferably from 0.1% to 25%. most preferably from 1% to i The composition is advantageously used as a granule or granules or pellets.

SGenerally, in use. the granule is capable of being carried-by a leaf cutter ant from the site of placement, the granule being generally cylindrical, about 1-4 mm in diameter preferably about 2 mm in diameter, and from 3-10 mm in length, preferably about 7 mm in lenath. The granule or pellet of the invention is substantially dustless. By substantially dustless is meanthaving a particles that do not rub off on the human d *u s~ ta l f ihand hen rubbed. Generally the pellets have less than P by weight ofIdust if the lin tre >t 1Ce 1in te liOll.

lhe present invention also pro ides for a new process by which to make a granule for ant baits which comprises the steps of: a) preparing a generally homogeneous mixture of the compound of formula (1) in the oil: b) mixing the product of step a and the fruit component; c) pelleting of the final mixture.

Optionally. the process may further comprise a step bl in which the starch component is added and mixed with the fruit component before the product of step a) is mixed.

The process of the present invention generally is effected at a temperature from ambient temperature to 100°C.

In the final pelleting step. the mixture of steps a and b is generally effected by loading the said mixture into a compressing and extruding device which produces the pellets of the invention.

The process of the invention also may optionally include a cooling step after Sthe pelleting step which allows the pellets of the invention to cool to ambient temperature.

1 20 The present invention also provides a commercial product which comprises the composition of the invention. In a particularly preferred aspect of the product. the there is provided a bag which contains from 5 to 50 grams of the composition of the invention, preferably from 7 to 20 grams of the composition. The bag is generally a plastics bag which sealably contains the composition. In general the bag is a sealed sachet. preferably a sachet of polyethylene which is capable of being cut by leaf-cutter ants. Generally the thickness of the bag is from 10 to 100 microns thick, preferably S* from 20 to 50 microns thick, most preferably from 25-40 microns thick.

The invention also relates to a method of controlling ants, particularly leafcutter ants by treatment of a locus with a composition or a product as defined supra.

The locus generally comprises an area where the said ants are moving or are expected to move. The area to be treated includes orchards, plantations, nurseries, forests. leaf- i cutter ant trails, fields where field crops grow, and other areas known to those skilled .I in the art ofcontro of leaf-cutter ants. Preferably the areai to e ireated comprises a Sleaf-cutter ant trail outside the area ol thc ;a nest. More specificall ,n ap!licaion el the composition is in a region of Irom I nim to 5t) cm from the trail or within 50 ll of a passage in thile earth which leads to tile nest.. The ant nest is generally known to those skilled in the art as an ant mound or a series of ant mounds that are comprised by the nest. Most advantageously, the composition is placed just outside the trails in individual doses of the composition, and generally spaced from each other so as to allow the leaf cutter ants various opportunities to take the composition to the nest.

Generally the amount of formulated product to be delivered to the locus is from about 0.01 to 50 milligrams per square meter, preferably from 0.1 to 10 mg/nm more preferably from 0.2 to 1 mg/m 2 The method of controlling ants. particularly leaf-cutting ants may also be effected by systematically distributing the sachets of the invention in a systematic way over a large area of forest. This particular embodiment of the invention is generally known as the MIPI method in Brazil.

The following non-limiting examples illustrate the invention.

""EXAMPLE 1 S" Nine compositions. sixty grams (60g) each, of the invention are made in the following manner by: a. dissolving 1.8 mg of Compound A in the soybean oil: b. mixing of the ground orange pulp and cornmeal; c. mixing to a generally homogeneous point the product of steps a and b: Sd. pelleting of the final mixture in a compression and extrusion device: e. cooling the pellets.

S The percentages of the ingredients are listed in Table 1. All the pellets have a final concentration of about 30 ppm by weight (0.003% by weight), the total amount of the ingredients adding to 100%. The resulting cylindrical pellets are generally about 7 mm long and 2 mm in diameter. Generally, the pellets of the invention are acceptable for long term storage in that they do not absorb large amounts of water: are I substaZ1uailI\ dustless and are _,en;:raII% hcai-resi-sunt and do not fragmnr.

I usannalxComnpositions I I Ild ]I in biQ I bclow are _eneraIK\ prel' rrcd.

I TABLE I Composition a weight of %eh of %1 weigzht of cornmeal orange bagasse soybean oil 907___5__ 4 20 76.5 1 9 V 93.5 1 1.

Example 2 I The pellets of Example I are dispersed around. the entrance of. a leaf-cutter ant nest which is about 50 ni in Surface area, at a rate of about 10 g m' (that is about 0.30 mz'n, of the active ini-redient) in aboutO 10 rarn amounts as a small hill of bait.

The granules are placed just along the side of (about 5 cm from) the trails of the ants.

After about 72 hours days there is substantially no activityv around the nest- There is little to no rejection of the bait by the ants.

~Example 3: Sealed polyethylene sachets of about 30 micron wall thickness containlinnQ grams of a composition of Example I are distributed in a Eucalyptus forest infested with leafcutter ants in a density, of about one sachet per 50 m2 to 100 in 2 After two ant activity and feeding on the Eucalyptus trees is reduced by '70 to Throughout this specification and the claims which follow, unless the -context requires; otherwise, the word "comprise",* and variations such as 'comprises' and 'com~prising", will be understood to imply the inclusion of a stated. integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

Claims

2-yl or haloalkyl;I 10 is alkvl or haloatkyI: o R 4 is selected from the gzroup ossiQo hydrogen. halogen. -N-\'R5R 6 -C(O)OGR 7 -S(O)mR7. alkyl- hialoalkvl, -0RS- -N-C(R 9 )(R 1 0) and -C(O)alkyl: Ri and R 6 are independently selected from a hvdrocen atom, alkvL. haloalkvl -C(O)alkvl, -C(O)0R 7 or Ri and R 6 form together a divalent alkivene radical which may be interrupted by one or more heteroatoms. preferably selected from oxygen. nitrogen and sulftur; R 7 is selected from alkyl and haloalkvl; R8 is selected from alkyl, haloalkyl.- and hydrogen; R 9 is selected from hydrogen and alkvl:. RIO is selected from phenyl or heteroaryl each of which is unsubstituted or substituted by one or more hydroxy. halogen. -0-alkyl. -S-alkvl, cyano. or alkyl or combinations thereof: X is scicctLcd troi Aircn ~d CN. R, R an N are In-lependentlk s electcd froi halogen or h\ dro'',n 01 CN or\CNO R. 1 is selected fro-m halogen. hiaioalkyli. haloalkoxy. -S0)CFs.-SF, n i ii q. r are independently selected from 0- 1. and 2: prvddthat when R I is methl. N. is haloalkxl. R 4 is NH 1 is Cl. P,3 IIs CF-. and X is N and provided that when is 4-i-dicvariolmidazol 2-N- .R 4 is C1. RI I is C1. RI 1 is C.an I-CCl a fruit component- 2. The COMPOSition according to Claim I wherein the fruit componient is an orang-e component.
3. A composition accordindg to Claim 2 wherein the orange component 13cori[Ses the peel audi or pulp of the orang~e. preferably a wherein the orance component IS in the formn ofa bagasse.
4. A composition according to anv one of the foregoing clainis whrin the compound of formula kl) has one or more of the following features wherein: R is CN: Ss1 P-4i -NIR 5 R 6 R~i and R 6 are independently selected from the hydrogen atom- alkyl, haloalkvl-. C(O)alkvl-. C(O)0R 7 X -5 is C-Rp--.or R 1 3, is selected from a halogen atomn. haloalkyl.haloaikoxy. and -SF 5 The composition according it.) anv one of the forecoinul claims dhecin the COmIpoLUnd of l'Ormula 1 is 5-amino-S-cyano- I 2.0-dichloro-4-
6. A composition according to any one of the foregoing. claims wherein the amount of compound of formula is from I g to 200 g per metric ton or the composition. preferably from 10 to 100 u per metric ton, most preferably from 20 gto AO per metric ton. Aopsitionl accordinu,- to anv one of the fore-oing, claims that further comprises a vegetable oil, preferably soybean oil. peantut oil. rapeseed oil or con il most preferably soyba i S. The composition according to claim 7 wherein the amount of th oil1 is from 0.01% to about 30% b% weight.
9. The composition according to any one of the forenoing claims which further comprises a starch component. preferably a farinaceous product. The composition of claim 9 wherein the starch component is a ground corn product. preferably cornmeal. II_ A method of controlling leaf-cutter ants by treatment of a locus with a compositon as defined in any one of claims 1 12 A method according to Claim I1I wherein the locus comprises an area *.where leaf-cutter ants, are moving or expected to move, preferably comprising a leaf- cutter ant trail.
13. A commercial product comprising thle comlposition ON' ny Otc claimis 1-10 aind Utilized bv the niethod according to an,, one 01 limtis 11-12. fI i: 13
14. A composition according to claim 1, or a method according to claim 11, substantially as hereinbefore described with reference to the Examples. The steps, features, compositions and compounds disclosed herein or referred to or indicated in the specification and/or claims of this application, individually or collectively, and any and all combinations of any two or more of said steps or features. DATED this FOURTEENTH day of OCTOBER 1998 Rhone-Poulenc Agro by DAVIES COLLISON CAVE Patent Attorneys for the applicant(s) ~I r liri r j ~i~ll nS_.i i-ii -i