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(12) United States Patent (10) Patent No.: US 6,528,079 B2 Podszun Et Al

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(12) United States Patent (10) Patent No.: US 6,528,079 B2 Podszun Et Al US006528079B2 (12) United States Patent (10) Patent No.: US 6,528,079 B2 PodsZun et al. (45) Date of Patent: *Mar. 4, 2003 (54) SHAPED BODIES WHICH RELEASE 4,845,106 A 7/1989 Shiokawa et al. .......... 514/342 AGROCHEMICALACTIVE SUBSTANCES 4,849,432 A 7/1989 Shiokawa et al. .......... 514/341 4.882,344 A 11/1989 Shiokawa et al. .......... 514/342 (75) Inventors: Wolfgang Podszun, Köln (DE); Uwe 4.914,113 A 4/1990 Shiokawa et al. .......... 514/333 Priesnitz, Solingen (DE); Jirgen 4,918,086 A 4/1990 Gsell .......................... 514/351 4,918,088 A 4/1990 Gsell .......................... 514/357 Hölters, Leverkusen (DE); Bodo 4.948.798.2- Y - A 8/1990 Gsell .......................... 514/275 Rehbold, Köln (DE); Rafel Israels, 4,963,572 A 10/1990 Gsell .......................... 514/357 Monheim (DE) 4,963,574. A 10/1990 Bachmann et al. ......... 514/357 4,988,712 A 1/1991 Shiokawa et al. .......... 514/340 (73) Assignee: Bayer Aktiengesellschaft, Leverkusen 5,001,138 A 3/1991 Shiokawa et al. .......... 514/342 (DE) 5,034.404 A 7/1991. Uneme et al. .............. 514/365 5,034,524 A 7/1991 Shiokawa et al. .......... 544/124 (*) Notice: This patent issued on a continued pros- 5,039,686 A 8/1991 Davies et al. ............... 514/341 ecution application filed under 37 CFR 5,049,571. A 9/1991 Gsell .......................... 514/345 1.53(d), and is subject to the twenty year SE A :1: S. - - - - - - - -tal.5 E.s pass" provisions of 35 U.S.C. 5,166,1642Y- - - 2 A 11/1992 NanjoOKaWa et al. C ................a 514/357 Z. 5,175,301 A 12/1992 Minamida et al. .......... 546/272 - 5,192,778 A 3/1993 Kodaka et al. ............. 514/341 Subject to any disclaimer, the term of this 5201925 A 4/1993 Itzel et al. .......... ... 47/58 patent is extended or adjusted under 35 5,204,360 A 4/1993 Shiokawa et al. .......... 514/342 U.S.C. 154(b) by 9 days. 5,214,152 A 5/1993 Minamida et al. .......... 548/181 5,256,679 A 10/1993 Minamida et al. .......... 514/357 (21) Appl. No.: 09/194,648 5,264,584. A 11/1993 Kodaka et al. .......... 548/332.5 1.-1. 5,280,123. A 1/1994 Nanjo et al. ................ 548/111 (22) PCT Filed: May 22, 1997 5,298,507 A 3/1994 Shiokawa ................... 514/256 (86) PCT No.: PCT/EP97/02624 (List continued on next page.) S371 (c)(1), FOREIGN PATENT DOCUMENTS (2), (4) Date: Dec. 1, 1998 DE 34.32573 4/1985 (87) PCT Pub. No.: WO97/46094 DE 3639877 5/1988 PCT Pub. Date: Dec. 11, 1997 DE 3712307 10/1988 (65) Prior Publication Data (List continued on next page.) OTHER PUBLICATIONS US 2002/0061323 A1 May 23, 2002 Caplus Abstract, AN 1972:415375, Suto et al. 1972.* (30) Foreign Application Priority Data Database WPI, Section Ch, Week 8315, Derwent Publica Jun. 4, 1996 (DE) ......................................... 196 22 355 tions Ltd., London, GB; Class A97, AN 83-36012K, XP002043617 & JP 58 039 602A (Nitto Electric Ind. Co.) (51) Int. Cl." ........................ A01N 25/08: A01N 25/00; Mar. 8, 1983. A61K 9/14; A61 K9/50 (52) U.S. Cl. ....................... 424/409; 424/405; 424/408; Primary Examiner Russell Travers 424/489; 424/501 Assistant Examiner. Shengjun Wang (58) Field of Search ................................. 424/405, 409, (74) Attorney, Agent, or Firm Joseph C. Gil; John E. 424/489, 501, 408 Mrozinski, Jr.; Richard E. L. Henderson (57) ABSTRACT (56) References Cited The present invention relates to shaped articles whichrelease U.S. PATENT DOCUMENTS agrochemical active compounds, are used for treatment of 3,968.201. A * 7/1976 Ryde et al. ................. 424/437 Woody plants and 4,531,002. A 7/1985 Harris ......................... 544/54 are employed in a hollow preformed in the Woody plant, 4,590,272 A 5/1986 Shiokawa et al. ... 544/335 are of a volume which fills the volume of the hollow to the 4,606,862 A 8/1986 Harris 260/402.5 4,647,570 A 3/1987 Shiokawa et al. .......... 514/341 extent of 10 to 95%, 4,678,795. A 7/1987 Shiokawa et al. .......... 514/341 are of a Volume which does not increase during the period 4,680,294 A 7/1987 Shiokawa et al. .......... 514/256 of use to the extent that the preformed hollow Space is 4,687.845 A 8/1987 Hollowood et al. .......... 544/54 filled completely, 4,693.887. A * 9/1987 Shah ................... ... 424/486 comprise 4,742,060 A 5/1988 Shiokawa et al. .......... 514/252 4,772,620 A 9/1988 Shiokawa et al. .......... 514/341 a) agrochemical active compounds, 4,774,247 A 9/1988 Shiokawa et al. .......... 514/256 b) water-insoluble thermoplastically processable 4,795,641. A 1/1989 Kashdan .............. ... 424/438 polymers, 4,803.277 A 2/1989 Shiokawa et al. .......... 514/332 c) water-Soluble polymers and 4,806,553 A 2/1989 Shiokawa et al. .......... 514/332 d) is appropriate further auxiliaries. 4,812,454 A 3/1989 Shiokawa et al. .......... 514/256 4,812,571 A 3/1989 Shiokawa et al. .......... 546/296 7 Claims, No Drawings US 6,528,079 B2 Page 2 U.S. PATENT DOCUMENTS EP O 524 831 1/1993 5,343,653 A 9/1994 Itzel et al. ................... 25415 E. so : y o AoN250 5,384.324 A 1/1995 Shiokawa et al. ... 514/365 EP O 428 941 5/1995 5,405,961 A 4/1995 Nanjo et al. ..... ... 544/243 EP O 375 907 1/1996 5,428,032 A 6/1995 Shiokawa et al. ....... 514/226.8 JP 63287764 11/1988 5,461,167 A 10/1995 Shiokawa et al. ... 548/202 JP 63307857 12/1988 5,536,505 A 7/1996 Wilson et al. ... ... 424/486 5,580.889. A 12/1996 Shiokawa et al. ... 514/343 2207083 8/1990 5,665,713 A * 9/1997 Camden .......... ... 514/76 JP 322O176 9/1991 5,679,618 A * 10/1997 Kocur ........................ 504/116 JP 3246.283 11/1991 5,750,704 A 5/1998 Shiokawa et al. ....... 546/275.1 JP 3255O72 11/1991 5,935,981 A 8/1999 Minamida et al. .......... 514/365 JP 3279359 12/1991 JP 40093.71 1/1992 FOREIGN PATENT DOCUMENTS WO 91/O3940 4/1991 WO 91/04732 4/1991 RE 3. RC WO 91/17659 11/1991 EP O 344 117 11/1989 WO 94/O8455 4/1994 EP O404 727 12/1990 EP O 453 112 10/1991 * cited by examiner US 6,528,079 B2 1 2 SHAPED BODIES WHICH RELEASE The volume of the shaped article fills the hollow form to AGROCHEMICALACTIVE SUBSTANCES the extent of 10 to 95%, preferably to the extent of 50 to 90%. The shape of the body is not critical for the activity, This application is a 371 of PCT/EP97/02624, filed May and it can be rod-shaped, cylindrical or conical. Conical 22, 1997, which claim the foreign priority of Germany bodies with a base area which corresponds to the diameter of the hollow form can be employed such that the hollow 19622355.5, filed Jun. 4, 1996. form is closed off tightly. However, it is also possible to establish the tight closure with a closing cap or a closing TECHNICAL FIELD OF THE INVENTION paste, for example of a commercially available grafting wax. The invention relates to shaped articles which release Agrochemical active compounds which may be men agrochemical active compounds, are used for treatment of tioned are insecticides, fungicides and herbicides. Woody plants and comprise a water-insoluble thermoplasti Insecticides which may preferably be mentioned are cally processable polymer, a water-Soluble polymer and one organic phosphorous compounds, Such as phosphoric acid or more agrochemical active compounds. esters, carbamates, pyrethroids, urea derivatives, Such as benzoyl ureas, triazines, agonists or antagonists of the BACKGROUND OF THE INVENTION 15 nicotinic acetylcholine receptors of insects. Juvenile hor mones and juvenoid Synthetic compounds we, for example, The incorporation of agrochemical active compounds into pyriproxyfen, methoprene, hydroprene, are also to be men polymers is known, for example from DE-A 4432 126, WO tioned. 91/4732, WO 94/8455, EP-A524 831, WO 91/3940, EP-A The pyrethroids include: 404 727, EP-A 254 196, JP-A58/39 602. Alethrin=2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1- Polymer mixtures of a water-containing hydrophilic poly yl 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane mer and water-insoluble thermoplastic polymer are known carboxylate. from EP-A 0 344 118 as a carrier material for active Barthrin=(6-chloro-1,3-benzodioxol-5-yl)-methyl 2,2- compounds, the shaped articles obtained from this material dimethyl-3-(2-methyl-1-prope nyl)-cyclopropane having an improved dimensional Stability in damp air. In 25 carboxylate. water, these materials Swell very Severely and as a result Bioresmethrin=5-(phenyl-methyl)-3-furanyl-methyl 2,2,3- increase their volume Several-fold. (2-methyl-1-propenyl)-carboxylate. Brome thrin=(5-benzyl-3-furyl)methyl 2-(2,2- A method for plant treatment in which shaped articles of dibromovinyl)-3,3-dimethylcyclopropane-carboxylate agrochemical active compounds and a Solid carrier are Cycloethrin=3-(2-cyclopenten-1-yl)-2-methyl-4-oxo-2- introduced into the sap flow of plants is known from EP-A cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-propenyl)- 564 945. cyclopropane-carboxylate. Dimethrin=2,4-dimethylbenzyl 2,2,3-(2-methyl-1- SUMMARY OF THE INVENTION propenyl)-carboxylate The present invention relates to shaped articles which 35 Pyresmethrin=3-(5-benzyl-3-furyl)-methylmethyl trans release agrochemical active compounds, are used for treat (+)-3-carboxy-C.2,2-trimethylcyclopropane-acrylate.
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