WO1998021945B1 - Agricultural pesticide formulations - Google Patents
Agricultural pesticide formulationsInfo
- Publication number
- WO1998021945B1 WO1998021945B1 PCT/US1997/021514 US9721514W WO9821945B1 WO 1998021945 B1 WO1998021945 B1 WO 1998021945B1 US 9721514 W US9721514 W US 9721514W WO 9821945 B1 WO9821945 B1 WO 9821945B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pestlcldal
- boron
- formulation
- organic solvent
- agricultural
- Prior art date
Links
- 239000003090 pesticide formulation Substances 0.000 title 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract 26
- 229910052796 boron Inorganic materials 0.000 claims abstract 26
- 239000000463 material Substances 0.000 claims abstract 22
- 239000000203 mixture Substances 0.000 claims abstract 21
- 238000009472 formulation Methods 0.000 claims abstract 19
- 239000000575 pesticide Substances 0.000 claims abstract 12
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims abstract 9
- 229940067606 Lecithin Drugs 0.000 claims abstract 9
- 239000000787 lecithin Substances 0.000 claims abstract 9
- 235000010445 lecithin Nutrition 0.000 claims abstract 9
- 239000003960 organic solvent Substances 0.000 claims abstract 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 6
- 241000196324 Embryophyta Species 0.000 claims 9
- 239000002131 composite material Substances 0.000 claims 8
- -1 alkali metal borate Chemical class 0.000 claims 5
- 241000607479 Yersinia pestis Species 0.000 claims 4
- CLZJMLYRPZBOPU-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] CLZJMLYRPZBOPU-UHFFFAOYSA-N 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- 235000010339 sodium tetraborate Nutrition 0.000 claims 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 3
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N Boron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims 3
- 241000238631 Hexapoda Species 0.000 claims 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 3
- 235000010338 boric acid Nutrition 0.000 claims 3
- 239000004327 boric acid Substances 0.000 claims 3
- 239000004328 sodium tetraborate Substances 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper(II) hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 235000019198 oils Nutrition 0.000 claims 2
- 150000003904 phospholipids Chemical class 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- KAATUXNTWXVJKI-WSTZPKSXSA-N (1S)-cis-(alphaR)-cypermethrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-WSTZPKSXSA-N 0.000 claims 1
- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 claims 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N Alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims 1
- 241000512259 Ascophyllum nodosum Species 0.000 claims 1
- 229910011255 B2O3 Inorganic materials 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims 1
- PXRBHCKHCRNGSE-UHFFFAOYSA-N Calcium hexaboride Chemical compound [Ca+2].B123B45B67[B-]52B61[B-]743 PXRBHCKHCRNGSE-UHFFFAOYSA-N 0.000 claims 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N Carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
- 229960005286 Carbaryl Drugs 0.000 claims 1
- 239000005747 Chlorothalonil Substances 0.000 claims 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N Chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims 1
- YUAUPYJCVKNAEC-SEYXRHQNSA-N Cymiazole Chemical compound CC1=CC(C)=CC=C1\N=C/1N(C)C=CS\1 YUAUPYJCVKNAEC-SEYXRHQNSA-N 0.000 claims 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N Cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims 1
- 239000005946 Cypermethrin Substances 0.000 claims 1
- 239000005533 Fluometuron Substances 0.000 claims 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N Fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 239000005949 Malathion Substances 0.000 claims 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N Malathion Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims 1
- 235000019483 Peanut oil Nutrition 0.000 claims 1
- 229960000490 Permethrin Drugs 0.000 claims 1
- 229960005235 Piperonyl Butoxide Drugs 0.000 claims 1
- JBUKJLNBQDQXLI-UHFFFAOYSA-N Sodium perborate Chemical compound [Na+].[Na+].O[B-]1(O)OO[B-](O)(O)OO1 JBUKJLNBQDQXLI-UHFFFAOYSA-N 0.000 claims 1
- 229960005322 Streptomycin Drugs 0.000 claims 1
- 240000008529 Triticum aestivum Species 0.000 claims 1
- XLGKQYORSIIXIV-UHFFFAOYSA-N [Ca+2].OB(O)O.OB(O)O.OB([O-])[O-] Chemical compound [Ca+2].OB(O)O.OB(O)O.OB([O-])[O-] XLGKQYORSIIXIV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- MGFANRQPPVHYBW-UHFFFAOYSA-N barium(2+);boric acid;hydrogen borate Chemical compound [Ba+2].OB(O)O.OB(O)O.OB([O-])[O-] MGFANRQPPVHYBW-UHFFFAOYSA-N 0.000 claims 1
- 239000000828 canola oil Substances 0.000 claims 1
- 235000019519 canola oil Nutrition 0.000 claims 1
- 150000001747 carotenoids Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 235000012343 cottonseed oil Nutrition 0.000 claims 1
- 239000002385 cottonseed oil Substances 0.000 claims 1
- 229960005424 cypermethrin Drugs 0.000 claims 1
- 230000002939 deleterious Effects 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- LVSJLTMNAQBTPE-UHFFFAOYSA-N disodium tetraborate Chemical compound [Na+].[Na+].O1B(O)O[B-]2(O)OB(O)O[B-]1(O)O2 LVSJLTMNAQBTPE-UHFFFAOYSA-N 0.000 claims 1
- CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 claims 1
- RSCACTKJFSTWPV-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 RSCACTKJFSTWPV-UHFFFAOYSA-N 0.000 claims 1
- KRHIGIYZRJWEGL-UHFFFAOYSA-N dodecapotassium;tetraborate Chemical compound [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] KRHIGIYZRJWEGL-UHFFFAOYSA-N 0.000 claims 1
- YLYFOJDUNYYVKY-UHFFFAOYSA-N dodecasodium;tetraborate;pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] YLYFOJDUNYYVKY-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000749 insecticidal Effects 0.000 claims 1
- 229960000453 malathion Drugs 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- GDISSJBTLJQKKS-UHFFFAOYSA-A pentadecaazanium;pentaborate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] GDISSJBTLJQKKS-UHFFFAOYSA-A 0.000 claims 1
- PYUBPZNJWXUSID-UHFFFAOYSA-N pentadecapotassium;pentaborate Chemical compound [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] PYUBPZNJWXUSID-UHFFFAOYSA-N 0.000 claims 1
- VPOLVWCUBVJURT-UHFFFAOYSA-N pentadecasodium;pentaborate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] VPOLVWCUBVJURT-UHFFFAOYSA-N 0.000 claims 1
- 235000015424 sodium Nutrition 0.000 claims 1
- 229960001922 sodium perborate Drugs 0.000 claims 1
- 239000003549 soybean oil Substances 0.000 claims 1
- 235000012424 soybean oil Nutrition 0.000 claims 1
- 235000020238 sunflower seed Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 235000019529 tetraterpenoid Nutrition 0.000 claims 1
- 230000002588 toxic Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims 1
- 235000021307 wheat Nutrition 0.000 claims 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N γ-lactone 4-hydroxy-butyric acid Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 244000037666 field crops Species 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 239000003791 organic solvent mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Abstract
The present invention relates generally to the method for the production of liposomal microencapsulated boron-containing products to be used for agricultural formulations. More specifically, a new method of production of liposomal microencapsulated is disclosed for active agents such as pesticides. A lecithin is mixed with an organic solvent in a certain proportion so as to provide solutions with varied levels of solubilized lecithin. The particular solvent being used will depend on the amount of active agent (AA) desired in the final solution. The formulation of the lecithin/organic solvent mixture is then allowed to settle. After settling, the top layer is separated and saved, while the bottom layer is discarded. An AA is then added to form a concentrate that is added to water for vesicle formation. Boron-containing materials formulated according to the invention may now be applied to agricultural field crops and fruit.
Claims
47
AMENDED CLAIMS
[received by the International Bureau on 19 May 1998 (19.05.98); original claims 1, 6, 9-14, 16 and 18-20 amended; remaining claims unchanged (5 pages)]
1. A slow release pesticide composite formulation comprising: a) a boron-containing pesticide material in an amount sufficient to control pests which have a deleterious effect on agricultural crops, and b) a slow release liposomal carrier material bound to said boron-containing pestlcldal material including encapsulated agricultural pesticide effective to release said pestlcldal material at a rate sufficient to provide pestlcldal activity for protecting an agricultural crop without adversely affecting said crop, c) said encapsulated agricultural pesticide including a lipid vesicle having a phospholipid material derived from plant lecithin as its lipid source.
2. λ pesticide composite formulation as defined in claim 1 wherein said boron-containing material is a borate.
3. A pesticide composite formulation as defined in claim 2 wherein said borate is disodium octaboratβ tβtrahydrate.
4. A pesticide composite formulation as defined in claim 1 wherein the total amount of said boron-containing pestlcldal material present in said formulation is sufficient to be otherwise toxic to said crop if said slow release carrier material were not bound to said pestlcldal material -
48
5. A pesticide composite formulation as defined in claim 1 wherein said boron-containing pestlcldal material is effective to destroy plant-eating insects located on agricultural plant crops.
6. A prepackaged boron product comprising: a) a boron-containing material including a form of pestlcldal boron in sufficient amounts to destroy plant- eating Insects when the prepackaged boron product is mixed with water and sprayed onto agricultural plant crops, b) said amounts of boron-containing material being in solution with an organic solvent having a saturation level amount of plant lecithin in solution to form an organic solvent solution containing no undissolved portion, c) said prepackaged boron product being effective to form a slow release pesticide composite formulation including a phospholipid material derived from said plant lecithin when mixed with water.
7. A boron product as defined in claim 6 wherein said organic solvent is ethylene glycol.
8. A boron product as defined in claim 6 wherein said organic solvent solution includes a surfactant.
9. A boron product as defined in claim 6 wherein said boron-containing material is disodium octaborate tβtrahydrate in an amount sufficient to form a concentration of about 2 pounds of disodium octaborate tetrahydratθ being in solution in each gallon of said boron product .
49
10. A boron product as defined in claim 6 wherein said pestlcldal boron in solution is in a weight to weight ratio in the range of 500 parts per million to 2.5 pounds in each gallon of said boron product.
11. A boron product as defined in claim 6 wherein said boron-containing material includes an effective amount of an insecticidal boron in solution based on elemental boron content of up to about 5.5% by weight.
12. A pestlcldal formulation comprising: a) a pestlcldal material in an amount sufficient to effect pestlcldal activity when the pestlcldal formulation is mixed with water and sprayed onto vegetation, b) said amount of pestlcldal material being dissolved in an organic solvent solution including an organic solvent having a saturation level amount of plant lecithin in solution to form a pestlcldal solvent mixture having no undissolved portion, c) said pestlcldal solvent mixture being effective to form a slow release pesticide composite including liposomal encapsulated pestlcldal material when Bald pestlcldal solvent mixture is mixed with water.
13. A pestlcldal formulation as defined in claim 12 wherein said pestlcldal material is boric oxide, metaborlc acid, sodium borate, disodium octaborate, disodium octaborate tetrahydratθ, boron trioxide, anhydrous boric acid, borax, borax pentahydrate, borax decahydrate, a mixture of borax and boric acid, boric acid, sodium etaborate, sodium perborate, sodium tetraborate pentahydrate, sodium pentaborate, sodium pentβborate with anhydrous borax, potassium tetraborate, potassium pentaborate, ammonium biborate,
50
ammonium pentaborate, an organo etallic compound of boron, calcium boride, ulextile, colemanite, barium triborate, or calcium triborate.
14. A pestlcldal formulation as defined in claim 12 wherein said pestlcldal material is an alkali metal borate, an alkaline earth metal borate or an alkali metal borohydride.
15. A pestlcldal formulation as defined in claim 12 wherein said organic solvent solution includes carotenoid in an amount sufficient to control the ultraviolet degradability of said slow release pesticide composite when said formulation is disposed on said vegetation.
16. A pestlcldal formulation as defined in claim 12 wherein said organic solvent is ethylene glycol, acetone, 100% denatured anhydrous ethanol, dimethylformamide, gamma butyrolactone, methylβne chloride, or N-methyl pyrrolidone.
17. A pestlcldal formulation as defined in claim 12 wherein said plant lecithin is derived from soybean oil, cottonseed oil, canola oil, wheat oil, kelp, peanut oil, or sunflower seed oil.
16. A pestlcldal formulation as defined in claim 12 wherein said plant lecithin has a phosphatldylcholine content in the range of from about 5% to about 50% by weight.
19. A pestlcldal formulation as defined in claim 12 wherein said pestlcldal material is a borate, alachlor, alphamethrin, atrazlne, carbaryl, chlorothalonil, cymiazole, cupric hydroxide, cypermethrin, S-βthyl dipropylthiocarbamatθ, fluometuron, lambda oyhalothrin, permethrin, piperonyl butoxide, streptomycin, malathion, or triflurβlln.
20. A method for controlling the growth of or destroying agricultural pests including weeds, insects, fungi, and bacteria, said method comprising the step of bringing into contact with the agricultural pests an effective amount of the pestlcldal formulation of claim 12 mixed with water to control the growth of or destroy agricultural pests.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9911888A GB2334213B (en) | 1996-11-22 | 1997-11-24 | Slow release boron pesticides |
| AU53619/98A AU5361998A (en) | 1996-11-22 | 1997-11-24 | Agricultural pesticide formulations |
| CA002272474A CA2272474A1 (en) | 1996-11-22 | 1997-11-24 | Agricultural pesticide formulations |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/754,859 US5958463A (en) | 1991-07-29 | 1996-11-22 | Agricultural pesticide formulations |
| US08/754,859 | 1996-11-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998021945A1 WO1998021945A1 (en) | 1998-05-28 |
| WO1998021945B1 true WO1998021945B1 (en) | 1998-07-09 |
Family
ID=25036673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/021514 WO1998021945A1 (en) | 1996-11-22 | 1997-11-24 | Agricultural pesticide formulations |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5958463A (en) |
| AU (1) | AU5361998A (en) |
| CA (1) | CA2272474A1 (en) |
| GB (1) | GB2334213B (en) |
| WO (1) | WO1998021945A1 (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| KR100834965B1 (en) * | 2001-10-10 | 2008-06-03 | 에스케이케미칼주식회사 | Pesticide formulation composed of natural components |
| ITMI20012269A1 (en) * | 2001-10-29 | 2003-04-29 | Larderello Spa | PROCESS OF PRODUCTION OF A BORON SALT AND ITS USE IN AGRICULTURAL FIELD |
| US20030091662A1 (en) * | 2001-11-09 | 2003-05-15 | Ruth Lipman | Apparatus, method and composition for repelling animals |
| US6881247B2 (en) * | 2003-01-09 | 2005-04-19 | Vernon H. Batdorf | Protective barrier coating composition |
| TW200510051A (en) * | 2003-06-12 | 2005-03-16 | Matsushita Electric Ind Co Ltd | Air cleaner, functional filter and method of manufacturing the filter, air cleaning filter, and air cleaner device |
| US20050232973A1 (en) * | 2004-04-19 | 2005-10-20 | Makarand Gore | Systems and methods for preparation of pharmaceutical dosage using compositions containing aqueous vesicles |
| WO2007034275A2 (en) * | 2005-09-19 | 2007-03-29 | Battelle Uk Limited | Formulations for improved stability of pest control agents |
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| ES2324809B1 (en) * | 2008-02-13 | 2010-05-28 | Consejo Superior De Investigaciones Cientificas | SLOW RELEASE FORMULATIONS OF RESPECTFUL PESTICIDES WITH THE ENVIRONMENT. |
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| CA2859731C (en) | 2011-12-30 | 2016-03-15 | Gordon Murray | Pentachlorophenol/borate compositions and uses thereof |
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| US11039617B2 (en) | 2013-01-30 | 2021-06-22 | Agrofresh Inc. | Large scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness |
| US10264794B2 (en) | 2013-03-14 | 2019-04-23 | Stella-Jones Inc. | Compositions comprising unsaturated fatty esters and uses thereof |
| US9644103B2 (en) | 2013-07-03 | 2017-05-09 | Stella-Jones Inc. | Single step creosote/borate wood treatment |
| US9901098B2 (en) * | 2015-09-03 | 2018-02-27 | Tda Research, Inc. | Methods for plant protection |
| WO2017155879A1 (en) | 2016-03-07 | 2017-09-14 | Agrofresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| WO2017153993A1 (en) | 2016-03-09 | 2017-09-14 | Technion Research And Development Foundation Ltd. | Liposomal formulations and methods of using same in agriculture |
| CN112469281B (en) * | 2018-05-15 | 2023-05-30 | 旗舰创业创新六公司 | Pest control composition and use thereof |
| MX2020012148A (en) * | 2018-05-15 | 2021-02-26 | Flagship Pioneering Innovations Vi Llc | Pathogen control compositions and uses thereof. |
| WO2021113283A1 (en) * | 2019-12-02 | 2021-06-10 | The Board Of Trustees Of The University Of Arkansas | Compositions and methods to reduce dicamba volatility and provide plant essential nutrients |
| PL244203B1 (en) * | 2021-07-22 | 2023-12-18 | Syvento Spolka Z Ograniczona Odpowiedzialnoscia | Liquid proliposome composition of plant protection products and method of manufacturing the composition |
| CN115444003A (en) * | 2022-08-29 | 2022-12-09 | 江苏科技大学 | Method for preparing high-drug-loading phoxim nano-structure lipid carrier based on micro-fluidic control |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US496110A (en) * | 1893-04-25 | Insecticide | ||
| US1911551A (en) * | 1933-05-30 | Clarence r | ||
| US360700A (en) * | 1887-04-05 | Insecticide | ||
| US890636A (en) * | 1908-04-15 | 1908-06-16 | Louis F Fride | Insecticide. |
| US907498A (en) * | 1908-09-12 | 1908-12-22 | Charles W Hicks | Insecticide. |
| US1029203A (en) * | 1912-03-07 | 1912-06-11 | Oscar R Loewenthal | Insectifuge. |
| US1635461A (en) * | 1925-03-18 | 1927-07-12 | Pacific Coast Borax Company | Method of treating fruit and solution therefor |
| US1757222A (en) * | 1927-12-28 | 1930-05-06 | Ig Farbenindustrie Ag | Mothproof material and process of making same |
| US1923004A (en) * | 1928-10-23 | 1933-08-15 | Robert T Judson | Insecticide |
| US1976905A (en) * | 1933-02-04 | 1934-10-16 | Thordarson William | Insecticide and fertilizer and method of manufacture |
| US2711367A (en) * | 1951-09-04 | 1955-06-21 | Sr Clifford A Parish | Weed killer containing borax |
| US2773757A (en) * | 1953-05-14 | 1956-12-11 | United States Borax Chem | Process and composition for application of sodium borate for vegetation control |
| US2770538A (en) * | 1954-08-11 | 1956-11-13 | Donald E Vierling | Liquid fertilizers |
| US2968590A (en) * | 1956-06-19 | 1961-01-17 | Sergent Lab Ets | Synergistic boric acid fungicidal compositions |
| US3009598A (en) * | 1959-02-05 | 1961-11-21 | Flightex Fabrics Inc | Fastener anchoring gun |
| US3007844A (en) * | 1959-04-13 | 1961-11-07 | Allg Holzimpragnierung Dr Wolm | Wood-preserving agent |
| US3012931A (en) * | 1960-03-23 | 1961-12-12 | Sokoloff Boris Theodore | Nematocidal composition |
| US3305298A (en) * | 1964-11-30 | 1967-02-21 | Chapman Chem Co | Protecting treatment for wood |
| US3531278A (en) * | 1967-03-20 | 1970-09-29 | United States Borax Chem | Process for preparing sodium borate compositions |
| US3560381A (en) * | 1968-04-30 | 1971-02-02 | United States Borax Chem | High density boron product comprising a mechanical mixture of boric oxide with anhydrous borax or sodium tetraborate pentahydrate |
| US3674458A (en) * | 1969-01-28 | 1972-07-04 | Robert I Schattner | Method for regulating plant growth |
| US3706161A (en) * | 1970-11-16 | 1972-12-19 | Clark E Jenson | Tree medication capsule |
| JPS5118501B2 (en) * | 1972-06-06 | 1976-06-10 | ||
| NZ189120A (en) * | 1977-12-16 | 1981-12-15 | Borax Holdings Ltd | Wood-preservative containing an alkali metal boate and a dithiocarbamate |
| US4873084A (en) * | 1978-07-24 | 1989-10-10 | Sallay Stephen I | Insecticidal composition |
| SU948366A1 (en) * | 1979-02-26 | 1982-08-07 | Симферопольский государственный университет им.М.В.Фрунзе | Method of injecting biologically active subtances into plants |
| NZ194071A (en) * | 1979-06-25 | 1982-05-25 | Manchem Ltd | Preserving timber using a metal-organic compound also containing boron |
| US4956129A (en) * | 1984-03-30 | 1990-09-11 | Ici Americas Inc. | Microencapsulation process |
| US4363798A (en) * | 1981-07-09 | 1982-12-14 | S. C. Johnson & Son, Inc. | Termite bait composition |
| US4610881A (en) * | 1981-08-14 | 1986-09-09 | Bechgaard Carl C | Protective composition with penetrating carrier |
| DE3225703C1 (en) * | 1982-07-09 | 1984-01-19 | A. Nattermann & Cie GmbH, 5000 Köln | Phospholipid concentrate and its use as an adjuvant for the manufacture and discharge of spray broths containing crop protection agents |
| US4721706A (en) * | 1983-02-28 | 1988-01-26 | A.E. Staley Manufacturing Company | Controlling grain insects with phosphatides |
| GB8321913D0 (en) * | 1983-08-15 | 1983-09-14 | Acacia Chem Ltd | Spray method |
| GB8429447D0 (en) * | 1984-11-21 | 1985-01-03 | Bio Kil Chemicals Ltd | Shaped bodies of boron compounds |
| US5225279A (en) * | 1985-04-30 | 1993-07-06 | Rohm And Haas Company | Solvent core encapsulant composition |
| US4855090A (en) * | 1987-03-13 | 1989-08-08 | Micro-Pak, Inc. | Method of producing high aqueous volume multilamellar vesicles |
| US4944950A (en) * | 1987-04-03 | 1990-07-31 | Bronislava Sakharova | Bait composition and insecticide |
| US5225278A (en) * | 1987-08-26 | 1993-07-06 | Rohm And Haas Company | Process for microencapsulation |
| US5269979A (en) * | 1988-06-08 | 1993-12-14 | Fountain Pharmaceuticals, Inc. | Method for making solvent dilution microcarriers |
| US5019312A (en) * | 1988-10-18 | 1991-05-28 | Huffy Corporation | Method for assembling a bicycle frame |
| US4959221A (en) * | 1988-11-14 | 1990-09-25 | Iris Holmes | Pest exterminating composition |
| US5160530A (en) * | 1989-01-24 | 1992-11-03 | Griffin Corporation | Microencapsulated polymorphic agriculturally active material |
| US5077057A (en) * | 1989-04-05 | 1991-12-31 | The Regents Of The University Of California | Preparation of liposome and lipid complex compositions |
| US5277914A (en) * | 1989-03-31 | 1994-01-11 | The Regents Of The University Of California | Preparation of liposome and lipid complex compositions |
| US5098483A (en) * | 1989-09-05 | 1992-03-24 | Spire Corporation | Methods of treating spherical surfaces |
| US4996053A (en) * | 1989-11-22 | 1991-02-26 | Hatcher Richard P | Bait for controlling darkling beetles, lesser metal worms and hide beetles |
| US5104664A (en) * | 1990-05-24 | 1992-04-14 | Nisus Corp. | Methods and compositions for retarding and eradicating infestation in trees and tree derived products |
| US5229366A (en) * | 1990-10-23 | 1993-07-20 | Fuji Photo Film Co., Ltd. | Peptide-containing polyethylene glycol derivatives and application thereof |
| US5256181A (en) * | 1991-03-28 | 1993-10-26 | Exxon Research And Engineering Company | Coatings with ionically and covalently crosslinked sulfonated polymers |
| US5310496A (en) * | 1991-06-18 | 1994-05-10 | Chute Chemical Company | Vegetable oil based paint removing compositions |
| ATE156728T1 (en) * | 1992-01-03 | 1997-08-15 | Ciba Geigy Ag | SUSPENSION OF MICRO CAPSULES AND METHOD FOR THE PRODUCTION THEREOF |
| US5648532A (en) * | 1993-06-03 | 1997-07-15 | The Regents Of The University Of California | Compositions for boron neutron capture therapy and methods thereof |
| US5525147A (en) * | 1994-02-22 | 1996-06-11 | Perma-Chink Systems, Inc. | Preventative treatment of wood |
| US5464613A (en) * | 1994-06-17 | 1995-11-07 | Ecolab, Inc. | Fat-based pest bait |
-
1996
- 1996-11-22 US US08/754,859 patent/US5958463A/en not_active Expired - Fee Related
-
1997
- 1997-11-24 WO PCT/US1997/021514 patent/WO1998021945A1/en active Application Filing
- 1997-11-24 AU AU53619/98A patent/AU5361998A/en not_active Abandoned
- 1997-11-24 GB GB9911888A patent/GB2334213B/en not_active Expired - Fee Related
- 1997-11-24 CA CA002272474A patent/CA2272474A1/en not_active Abandoned
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