AU594774B2 - Aqueous suspension concentrate compositions of pendimethalin - Google Patents
Aqueous suspension concentrate compositions of pendimethalin Download PDFInfo
- Publication number
- AU594774B2 AU594774B2 AU73357/87A AU7335787A AU594774B2 AU 594774 B2 AU594774 B2 AU 594774B2 AU 73357/87 A AU73357/87 A AU 73357/87A AU 7335787 A AU7335787 A AU 7335787A AU 594774 B2 AU594774 B2 AU 594774B2
- Authority
- AU
- Australia
- Prior art keywords
- pendimethalin
- agents
- formaldehyde
- composition according
- methyl
- Prior art date
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 89
- 239000005591 Pendimethalin Substances 0.000 title claims description 46
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical group CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 title claims description 46
- 239000007900 aqueous suspension Substances 0.000 title claims description 27
- 239000012141 concentrate Substances 0.000 title claims description 26
- 239000013078 crystal Substances 0.000 claims description 44
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000575 pesticide Substances 0.000 claims description 27
- 239000002518 antifoaming agent Substances 0.000 claims description 18
- 238000002844 melting Methods 0.000 claims description 18
- 230000008018 melting Effects 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 239000003755 preservative agent Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000375 suspending agent Substances 0.000 claims description 12
- 239000002562 thickening agent Substances 0.000 claims description 12
- 229920001285 xanthan gum Polymers 0.000 claims description 12
- 239000000230 xanthan gum Substances 0.000 claims description 11
- 235000010493 xanthan gum Nutrition 0.000 claims description 11
- 229940082509 xanthan gum Drugs 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 239000008098 formaldehyde solution Substances 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 239000000080 wetting agent Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 150000003871 sulfonates Chemical class 0.000 claims description 7
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 5
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 5
- -1 polyoxyethylene Polymers 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 5
- 244000215068 Acacia senegal Species 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 229920002907 Guar gum Polymers 0.000 claims description 4
- 229920000084 Gum arabic Polymers 0.000 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 4
- 239000000205 acacia gum Substances 0.000 claims description 4
- 235000010489 acacia gum Nutrition 0.000 claims description 4
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000665 guar gum Substances 0.000 claims description 4
- 235000010417 guar gum Nutrition 0.000 claims description 4
- 229960002154 guar gum Drugs 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000003801 milling Methods 0.000 claims description 3
- KANAPVJGZDNSCZ-UHFFFAOYSA-N 1,2-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)N=CC2=C1 KANAPVJGZDNSCZ-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- TYIHVCIQMMTVHE-UHFFFAOYSA-N methyl 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-methylbenzoate Chemical compound COC(=O)C1=CC(C)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 TYIHVCIQMMTVHE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 2
- 235000010234 sodium benzoate Nutrition 0.000 claims description 2
- 239000004299 sodium benzoate Substances 0.000 claims description 2
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 claims 9
- 229920002678 cellulose Polymers 0.000 claims 3
- 230000002335 preservative effect Effects 0.000 claims 3
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 235000010980 cellulose Nutrition 0.000 claims 2
- OADSZWXMXIWZSQ-UHFFFAOYSA-N 2-bromo-2-nitropropane Chemical compound CC(C)(Br)[N+]([O-])=O OADSZWXMXIWZSQ-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 230000003254 anti-foaming effect Effects 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229920002401 polyacrylamide Polymers 0.000 claims 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims 1
- 229920005646 polycarboxylate Polymers 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229920005552 sodium lignosulfonate Polymers 0.000 claims 1
- 239000004546 suspension concentrate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- RKZIPFOHRUCGGS-UHFFFAOYSA-N 4,5-dihydroimidazole-1-carboxylic acid Chemical class OC(=O)N1CCN=C1 RKZIPFOHRUCGGS-UHFFFAOYSA-N 0.000 description 1
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 4-amino-o-xylene Natural products CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 1
- YVWZBMHCQCVNFR-UHFFFAOYSA-N 4-chloro-2-methyl-1,2-thiazol-3-one Chemical compound CN1SC=C(Cl)C1=O YVWZBMHCQCVNFR-UHFFFAOYSA-N 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical group C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
i
A_:-.II
S"I
59 477 4 S F Ref: 27223 FORM COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: 7 3 -S7 7 Class Int Class Complete Specification Lodged: Accepted: Published: 4 4 4 4 4L Priority: Related Art: This 9cu11.idli coti'.(nAL, fl'4,W:''L61rtb m\de Stt' tirl 49( ud is cu(i' tt V\ Name and Address of Applicant: Actual Inventors: Address for Service: American Cyanamid Company One Cyanamid Plaza Wayne New Jersey UNITED STATES OF AMERICA LEONARD JOHN MOIAN and MARK BEL Spruson Ferguson, Patent Attorneys, Level 33 St Martins Tower, 31 Market Street, Sydney, New South Wales, 2000, Australia '4 Complete Specification for the invention entitled: AQUEOUS SUSPENSION CONCENTRATE COMPOSITIONS OF PENDIMETHALIN The following statement is a full description of this invp <tion, including the best method of performing it known to e/us 5845/3 -4M
ABSTRACT
An aqueous suspension concentrate cornposi',ion comprising, on a weight basis about 5.0% to 50.0% pendimethalin havinr, an orange crystal to yellow crystal ratio of about 4/96 up to totally of orange crystal form; about 0.05% to 50.0%~ of one or more secondary pesticide(s) having a melting point grea,'r than 70 0 C and consisting of Isoproturon, [N,N-dimetiiyl-NW-methoxy-N.-methyI urea]; Metoxuron, [N'-(-chloro-4methoxyphenyl)-N,N-.dimethylureaj; Chloroluron, [N'-(3-chloro-4-methylphenyl)-N,N-dimethylureal; Atrazine, E2,chloro-4-ethylamino-6--isopropylamlno-l ,3,5-trlazine, terbutylazine, 2-tert-butylamino-4-chloro-6-ethylamino-i ,3,5-triazlne and metalochior, 2-chloro-6-ethyl-N-(2-methoxy-lmethyl ethyl )aceto-o-toluidlde; 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin- Ott2 2-yl)-3-quinolinecarboxyllc acid and water soluble salts thereof; and S theisomeric mixture of 6-(4-iopcopyl-4-methyl-5-oxo--2-imidazolin-2-yl)-mtoluate and 2-(4--isoproplyl-.4-methyl-.5-oxo-2-imidazolin-2-yl~toluate; about 3.0% to 30.0% coformulants consisting of surfactants, dispersing agents, wetting agents, suspending agents, antifreezing agents, antifoctming agents, 0 t thickening agents or preservatives; and about 20,0% to 92.0% water.
R A TMR/998u 30338 .AQUEOUS SUSPENSION CONCENTRATE COMPOSITIONS OF ,H PENDIMETHALIN I BACKGROUND OF THE INVENTION Suspension concentrate or aqueous flowable pesticidal compositions are concentrated suspensions of water insoluble pesticides and mixtures of pesticides in aqueous systems. The present invention relates to stable such pendimethalin compositions.
Pendimethalin is a dinitroaniline that exists in polymorphic form, both in orange crystal form and yellow crystal form. U.S. Patents 4,082,537 and 4,150,969 address pendimethalin's unique formulation problems and provide ways to avoid formation and/or presence of the larger, orange crystal form (both incorporated herein by reference).
It is believed that the presence of pendimethalin in the orange macrocrystal form results in large elongated crystals in final formulations.
In order to formulate stable wettable powder compositions of pendimethalin, these two patents disclose utilizing a stabilized pendimethalin, tg stabilized by the addition of either sodium dialkyl
(C
6 sulfosuccinate or an ethoxylated 8- diamine.
_t i 1 r r J i -2- 1I
I
t
'I'
This technique maintains pendimethalin in the yellow crystal form which does not favor the formation of large elongated crystals in formulated product for the preparation of wettable powders. However, these patents fail to disclose ways to formulate pendimethalin as a stable suspension concentrate composition or aqueous flowable composition with orange crystal forms, which form is favored.
These aqueous compositions frequently contain about 10% to 80%, by weight of a solid pesticide or mixture of solid pesticides, thereby providing a method for handling those pesticides which are relatively water insoluble in an aqueous medium.
Since these types of compositions have the desirable characteristics of a thick liquid, they may be poured or pumped. Thus, some of the problems, like dusting that is possible in solid compositions of wettable powders and granulars, are avoided. Further, these aqueous-based concentrates also have the added advantage of not requiring the use of organic solvents, often present in emulsifiable concentrates.
For these reasons, it is desirable to formulate pesticides into suspension concentrates or aqueous flowables. However, such formulations have their own problems such as gelling, caking and settling, as well as problems because of the physical dnd chemical characteristics of the pesticide or mixture of pesticides. Pendimethalin is one of these pesticides that is somewhat difficult to formulate.
Oftentimes, when pendimethalin in the orange macrocrystal form is found in compositions, very large, elongated crystals (about 3000 microns in length) appear in final product, resulting in r i -~op~ t -j r 1 0 0 0 0 0 JO 8 0 0 00 a 00 0 00 00 0 P -3instability, difficulty in processing and unreliability of usage. Thus, formulating compositions wherein these elongated crystals do not develop is crucial to stability and necessary to obtain even distribution of active compound for application.
The problems associated with the development of suspension cuemleutrate compositions containing low melting active ing, tients, alone or in combination with higher melting active ingredients, are described in German Patent Application DE 3302648 Al. German Patent Application DE 3302648 Al tries to deal with the problems of an aqueous mixed dispersion of a low melting active ingredient in a solvent of phthalic acid C
I
-C
1 2 alkyl esters in combination with an aqueous suspension concentrate containing one or more 5i active ingredients as an alternative to a suspension concentrate containing low melting active ingredients, such as pendimethalinCN-(l-ethyl-propyl)-2,6-dinit'o- 3,4-xylidine]. The reason for the alternative approach of that application is the inability to prepare stable suspension concentrates by various techniques, including those of Eur opean Patent Application 0 33291.2 That EPO application describes insecticidal suspension concentrate compositions of phosalone and adjuvants which may be prepared with 25 molten insectLcide. These references do not address ways helpful to the development oC pendimethalin compositions which utilize the orange crystal form to produce a stable and evenly efficacious product.
It is an object of the present invention to provide stable aqueous concentrate compositions of the low melting pesticide, pendimethalin, in the orange crystal form either alone or in combination with secondary pesticide(s) in order to avoid the problem of formation of large elongated crystals of formulated pendiiothalin. These secondary pesticides are often 1 t
J
r I I .1 i I- i l L ICIIC PI ~-YICI- l~-~fl 01 00 0* 00 8 0 *0 00 0 I p p -4water insoluble or have melting points greater than
C.
It is a further object of this invention to provide such stable aqueous suspension concentrate compositions of pendimnethalin having a ratio of orange crystal to yellow crystal of 4:96 to totally (100%) orange crystal form.
Furthermore, an additional object of the present invention is to provide methods for preparing such stable aqueous suspension concentrate 10 compositions.
These and other objects will become more apparent by the detailed description of the invention provided herein.
15 SUMMARY OF THE INVENTION The present invention relates to st- le aqueous suspension concentrate compositions or aqueous flowable compositions comprising pendimethalin, alone or in combination with secondary pesticide(s).
Preferred compositions of the invention comprise, on a weight to volume basis about 5.0% to 50.0% pendimethalin having an orange cyrstal to yellow crystal ratio of about 4/96 up to totally 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s); about 3.0% to 30.0% of coformulants, such as surfactants, dispersing agents, wetting agents, antifreezing agents, antifoaming agents, thickening agents, suspending agents, preservatives and the like which do not solubilize or dissolve the pendimethalin; and about 20.0% to 92,0% water.
§-"cJsnivrxor cmzf M&&VBgV_=TI u- :r -H4--C44E Preferred stUs suspension 14. suspens o -rr~a+~occ*c-n-cc-srucuccu -rmr~-~--rrl-l-rrrrrrt~nt~t=rS~LFtLTt=t i 3
II~
i t *t 0,d os o 0 0
A
5 DETAILED DESCRIPTION OF THE INVENTION According to a first embodiment of this invention there is provided an aqueous suspension concentrate composition comprising, on a weight basis about 5.0% to 50.0% pendimethalin having an orange crystal to yellow crystal ratio of about 4/96 up to totally 100% of orange crystal form; about 0.05% to 50.0% of one or more secondary pesticide(s) having a melting point greater than 70 0 C and consisting of Isoproturon, [N,N-dimethyl-N'-methoxy--N'-methyl ureal; Metoxuron, [N'-(3-chloro-4methoxyphenyl)-N,N-dimethylurea]; Chloroluron, [N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea]; Atrazine, [2,chloro-4-ethylamino-6-isopropylamino-1,3,5-triazlne, terbutylazine, 2-tert-butylamino-4-chloro-6-ethylamino-1,3,5-triazine and metalochlor, 2-chloro-6-ethyl-N-(2-methoxy-lmethylethyl)aceto-o-toluidide; 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin- 2-yl)-3-quinolinecarboxylic acid and water soluble salts thereof; and theisomeric mixture of 6-(4-iopcopyl-4-methyl-5-oxo-2-imidazolin-2-yl)-mtoluate and 2-(4-isoproplyl-4-methyl-5-oxo-2-imidazolin-2-yl)toluate; about 3.0% to 30.0% coformulants consisting of surfactants, dispersing agents, wetting agents, suspending agents, antifreezing agents, antifoaming agents, thickening agents or preservatives; and about 20.0% to 92.0% water.
According to a second embodiment of this invention there is provided a method for the preparation of a stable aqueous suspension concentrate composition of pendimethalin, said method comprising: admixing, on a weight to volume ba.ls, about 5.0% to 50.0% pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s) in an aqueous solution containing surfactant(s), dispersing agent(s) or wetting agent(s) and antifoaming agents; milling the resulting mixture, wherein said average particle size of suspended particles is less than 20 microns; admixing thickening agents, suspending agents, antifreezing agents, preservatives and additional surfactants; and packaging the resulting aqueous suspension concentrate composition.
Coformulants Pesticides suitable for use in the compositions of the present invention include ureas, triazines, imndazolinones, alone or in combination, amongst just a few. Fungicides, insecticides and plant growth regulators which have melting points greater than amenable to the :nk j i
I
n 1 5A preparation of aqueous suspension concentrate compositions also may be used in the compositions of the present invention.
Additionally, water soluble pesticides, such as difenzoquat, amine salts, alkali or alkali metal salts of ioxynil, bromoxynil, phenoxy acetic acids, and imidazolinyl carboxylic acids such as 2-(4-isopropyl--4-methyl- 5-oxo-2-imidazolin-2-yl)-3-quino-linecarboxylic acid and the like may readily be incorporated into the stable aqueous suspension concentrate compositions of this invention.
Preferred such higher melting components for use in the aqueous suspension compositions of the invention containing pendimethalin include: t 4 4 4 i 4 44o T MR,98 _0VM~i8 1/ a p.- -6all be 00Li 0i &iLi L Isoproturon, [N,N-dimethyl-N'-(4-(l-methylethyl)-phenyl)urea]; Linuron, [N-(3,4-dichlorophenyl)-N'--methoxy-N'methyl urea]; Metoxuron, [N'-(3-chloro-4-methoxyphenyl)- N,N-dimethylurea]; Chiortoluron, EN'-(3-chloro-4-methylphenyl)-N,N-dimethylureaj; Atrazine, [2-chloro-4--ethylaini no-6-isopropyl amino-1, 3, 5- triaz ine; other secondary active components include terbutylazine, 2-tert-butylamino-li-chloro-6-ethylamino-1,3,5-triazine and meto- Jachior, 2-chloro-6 '-ethyl (2-metLhoxy- 1-methylethyl) acet-o-toluidide; Imidazolinone herbicides such as 2-(4-isopropyl-4-methyl-5-oxo--2-imidazolin-2-yl) -3quinolinecarboxylic acid and water soluble salts thereof, and the isomeric mixture of methyl 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl) -m-toluate and methyl 2-(4-isopropyl-4t-methyl-5-oxo-2-imidazolin-2-yl) toluate.
Surfactants (including dispersing agents and/or wetting agents) suitable in 'the aqueous suspension compositions of the invention containing pendimethalin include: ethylene oxide/propylene condensates; alkyl, aryl- and aryl, arylethoxylates and derivatives thereof; l1,gnosul fonates, cresol- and naphthalene- forinaldehyde condensates and sulfonates; pzolycarboxylates and derivatives thereof, and mixtures I.hereof.
in general, anionic polymerics, such as cresol iormaldehyde condens;.0es and their sulfoneites; naphtlialene formaldehlyde condensates and their sul~onates and lignosulfonates have been found to crystal formation during storage and as such are most preferred.
Suspending agents such as polysaccharide gums like Xanthan gum, guar gum; gum arabic and cell1ulose derivatives and the like are suitable for addItion i-n amounts of about 0,02% to on a weight to voluame hasis.
11 -7- Preservatives to prevent microbial spoiling in the compositions of the invention are included as necessary.
One example is a 38% formaldehyde solution. Other preservatives include methyl or propyl parahydroxybenzoate, 2-bromo-2-nitro-propane-1,3-diol, sodium benzoate, glutaraldehyde, 0-phenylphenol, benzisothiazolinones, chloro-2-methyl-4-isothiazolin-3-one, pentachlorophenol, 2-4-dichlorobenzylalcohol, or mixtures thereof and others known to those in the art. Siliconic antifoaming agents 0 are useful in the present compositions.
Antifreezing agents such as ethylene glycol, propylene glycol, other glycols, glycerine or urea may be added to the aqueous suspension concentrate compositions. Additional. surfactants, preservatives and thickening agents, such as clays, precipitated silicas, polyvinyl alcohol, polyvinyl-pyrrolidone, pol.yacrylamides and the like, may then be added, as can higher melting active components or a suspension concentrate containing other active components.
tt ,v 20 Process of Manufacturing Surprisingly, it has been found that stable aqueous suspension concentrate compositions of pendimethalin are prepared with at least 4.0% of the pendimethalin in the orange crystal form, contrary to what has been reported previously. In the present invention pendimethalin even in the large orange crystal form may be used to formulate stable aqueous (4 tsuspensions. Further, up to 100% of the pendimethalin may be present as the orange crystal form when preparing the compositions of the invention, whereas only the yellow crystal form was favored to avoid large elongated crystals of formulates of pend .methalin.
Thus, aqueous suspension concentrate composi.tions of pendimethalin alone or in combination with a second hiher melting pesticide(s) comprise on 0 U t) I be ad e to t e a u o s up n i n co c n r t *1 -8a weight to volume basis, about 5.0% to 50.0% of pendimethalin containing about 4.0% to 100% of the orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s) having a melting point greater than 70°C or being water soluble; about 3.0% to 30.0% coformulants as described hereinabove; and the remainder water to total the composition to 100%, The compositions of the present invention are readily prepared by adding solid pendimethalin to water that may contain some of the coformulants, such as the antifoaming agents and/or suspending agents; milling at ambient temperatures the resulting solid-aqueous mixture to obtain an average particle size of less than 20 microns, preferably 2 microns to 10 microns; and then adding, if desired, other coformulants such as thickening agents, antifreezing agents, surfactants, dispersing agents, wetting agents, suspending agents and preservatives.
The following examples further illustrate the present invention and are not limitative thereof.
EXAMPLES 1-9 Preparation of stable aqueous suspension concentrate compositions of pendimethalin An aqueous solution containing surfactant(s) 25 and antifoaming agents, and if desired, water soluble pesticides is prepared at ambient temperatures.
Solid pendimetllalin, having a minimum of 4% of the orange cirystal form, is added, and any other solid second pesticide having a melting point greater than 70 0 C may also be added.
This is milled to achieve the desired average paLrticle size of suspended particles of less than 20 microns, preferably less than 6 microns (2 microns to 6 microns). Then thickening agents, suspending agents, antifreezing agents, preservatives
I
-9and additional surfactants are admixed with the resulting mixture. Finally, this resulting stable aqueous suspension concentrat i composition is packaged.
Utilizing the above procedure yields the stable aqueous suspension concentrate compositions listed in Table I.
i L! 1* f 'TABLE I Stable aqueous suspension concentrate compositions (I wjv,,) Example Composition Pendimethal in (oranw--tgeIeow rat jo) Iscoprocuron Chlortoluron, Na- cresol-formldebyde su~lphona ted condensate Na naphthalene sulfonated condensate Zthylene oxide propyleneoxide copolymer tWa t lauryl sulphate .Zhanclzmine salt of varylarylethylene, oxide -hee iagYzol 1 2)3.6 68) 23.6 2 23-6 (32/68) 23.6 3 23.6 (32/68) 23-6 4 23,6 (24176) 23.6 5 23.6 (16184) 23-6 2 (8 2 6 7 8 3.6 23.6 20.0 192) (4/96) (46/54) 3-6 23.6 30.0 9 44.8 (low/.) 3-0 3-0 2-0 3.0 3.0 0,5 C.5, 3.0 8-0 8.0 8.0 3.0 3.0 3.0 2.0 0.5 0.5 8.0 8.,0 8.0 14 TABLE I (Continued~) Exampile CcOpOS irion Silica Siliconic artifoan Formaldehvde 38% solution Xanthan gum Water 1 2 3 4 5 6 7 8 9 2.0 0.5 0.125 0.05
QS
2.0 0.5 0-25 0.1
QS
2.0 0.5 0.25 0.1
QS
2.0 0.5 0.25 0.1
QS
2.0 0.5 0.25 0.1
QS
2.0 0.5 0.25 0.1
QS
2.0 0.5 0.25 0.1
QS
0.25 0.05
QS
Claims (13)
1. An aqueous suspension concentrate composition comprising, on a weight basis about 5.0% to 50.0% pendimethalin having an orange crystal to yellow crystal ratio of about 4/96 up to totally 100% of orange crystal form; about 0.05% to 50.0% of one or more secondary pesticioe(s) having a melting point greater than 70*C and consisting of Isoproturon, [N,N-dimethyl-N'-methoxy-N'-methyl urea]; Metoxuron, [N'-(3-chloro-4- methoxyphenyl)-N,N-dimethylureal; Chloroluron, [N'-(3-chloro-4-methyl- phenyl)-N,N-dimethylurea]; Atrazine, [2,chloro-4-ethylamino-6-isopropropyl- amino-1,3,5-triazine, terbutylazine, 2-ter-t-butylamino-4-chloro-6-ethyl- amino-1,3,5-triazine and metalochlor, 2-chloro-6-ethyl-N-(2-methoxy-1- methylethyl)aceto-o-toluidide; 2-(4-1sopropy1-4-methyl-5-oxo-2-imidazolin-
2-y1)-3-quinolinecarboxyllc acid and water soluble salts thereof; and thelsomeric mixture of 6-(4-1opcopyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m- toluate and 2-(4-isoproplyl-4-methyl-5-oxo-2-imidazolin-2-yl)toluate; about
3.0% to 30.0% coformulants consisting of surfactants, dispersing agents, wetting agents, suspending agents, antifreezing agents, antifoaming agents, thickening agents or preservatives; and auout 20.0% to 92.0% water, 2. A composition according to Claim 1, wherein said surfactants, dispersing agents or wetting agents are ethylene oxide/propylene oxide condensates; alkyl, aryl- and aryl, arly-ethoxylates; lignosulfonates; cresol-formaldehyde condensates and sulfonates thereof; naphthalene- formaldehyde condensates and sulfonates thereof; polycarboxylates and derivatives; and mixtures thereof. 3. A composition according to Claim 1 or Claim 2, wherein said suspending agents are polysaccharlde gums or cellulose derivatives.
4. A composition according to Claim 3, wherein said polysaccharide gums are Xanthan gum, guar gum, gum arabic, and mixtures thereof. A composition according to any one of Claims 1 to 4, wherein said antifreezing agents are ethylene glycol, propylene glycol, glycerine, urea, and mixtures thereof.
6. A composition according to any one of Claims 1 to 5, wherein said thickening agents are clays, precipitated silicas, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylamides, and mixtures thereof.
7. A composition according to any one of Claims 1 to 6, wherein said preservative is a 38% formaldehyde solution, methyl or propyl j; i Ebb-,L- LI -13 parahydroxybenzoate, 2-bromo-2-nitro-propane- ,3-diol, sodium benzoate, glutaraldehyde, 0-phenyphenol benzisothiazolinones, 5-chloro-2-methyl-4- i sothiazol n-3-one, pentachloropherol 2-4-dichi orobenzyl alcohol or mixtures thereof.
8. A composition according to any one of Claims 1 to 7, wherein said antifoaming agent is a siliconic antifoaming agent.
9. A composition according to Claim 8, comprising, on a weight to volume basis: about 5.0% to 50.0% pendimethalin with 10% of the pendimethalin, on a weight to weight basis, of the orange crystal form; about 0% to 50.0% one or more secondary pesticide(s) having a melting point greater than 70°C or being water soluble; cresol-formaldehyde condensates and sulfonates thereof, naphthalene-formaldehyde condensates and sulfonates thereof, lignosulfonates, and mixtures thereof; about 0.05% to 2.5% Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% S* ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming !:0oo agent; about 0.05% to 2.0% thickening agent; about 0.05% to 0 o *Oo preservative; and the remainder water to total said composition to 100%. A composition according to Claim 9, comprising, on a weight to ,i volume basis: about 20.0% to 40.0% pendimethalin; about 3.0% to 5.0% sodium I cresol-formaldehyde condensate or sodium cresol-formaldehyde glycol or Surea; about 0.1% to 1.0% siliconic antifoaming agent; about 0.1% to 0.3% Xanthan gum; about 0.2% to 1.0% of a 38% formaldehyde solution; and about i 48.3% to 79.4% water. I 11. A composition according to Claim 10, comprising, on a weight to volume basis: 40.0% pendimethalin; 5.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% ethylene glycol; 0.5% siliconic antifoaming agent; 0,2% Xanthan gum; 0.5% of a 38% formaldehyde solution; and 51.4% I |water.
12. A composition according to Claim 9, comprising, on a weight to volume basis: 27.3% penditethalin; 18.2% atrazine; 3.4% sodium cresol- formaldehyde sulphonated condensate; 5.8% urea; 1.34% polyalkylene glycol ether and polyoxyethylene alkylaryl ether; 0.9% siliconic antifoaming agent; 0.2% Xanthum gum; 0.5% of a 38% formaldehyde solution; and 48.9% water.
13. A composition according to Claim 9, comprising on a weight to volume basis: 23.6% pendimethalin; 23.6% Isoproturon; 3.0% sodium cresol- rM R/98 u Vo Uy^ YU^ 4 '4 44 444 4 4 *P 4 444 '44 40 44 4 4 04 44 *a 4 o '4 44l '44 4 '404 14 formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; ethylene oxide-propylene oxide copolymer; 2.0% silica; 0.5% siliconic antifoaming agent; 0.1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and 43.6% water.
14. A composition according to Claim 9, comprising on a weight to volume basis: 30.0% pendimethalin; 5.0% of the water-soluble ammonium salt of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3=-quinolinecarboxylic acid; 4.0% sodium lignosulphonate; 8.0% ethylene glycol, 0.5% siliconic antifoaming agent; 0.75% silica; 0.1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and 58.1% water. A composition according to Claim 9, comprising, on a weight to volume basis: 20.0% pendimethalin; 30.0% chlortoluron; 3.0% sodium cresol- formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; ethylene oxide-propylane oxide copolymer; 0.5% siliconic antifoaming agent; 2.0% silica; 0.05% Xanthan gum; 0.25% of a 38% formaldehyde solution; and
41.1% water. 16. A composition according to Claim 9, comprising, on a weight to volume basis: 26.0% pendimethalin; 12.5% of an isomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methy -5-oxo-2-imidazol in-2-yl)-p-toluate; 3.0% sodium cresol-formaldehyde condensate; 1.3% triethanolamine salt of polyarylaryl- ethoxylate phosphate; 6.0% alkylphenolethoxylate; 5.0% ethylene glycol; 0.4% siliconic antifoaming agent; 2.0% silica; 0,1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and 49.6% water. 17. A method for the preparation of a stable aqueous suspension concentrate composition of pendimethalin, said method comprising: admixing, on a weight to volume basis, about 5.0% to 50.0% pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s) in an aqueous solution containing surfactant(s), dispersing agent(s) or wetting agent(s) and antifoaming agents; milling the resulting mixture, wherein said average particle size of suspended particles is less than 20 microns; admixing thickening agents, suspending agents, antifreezing agents, preservatives and additional surfactants; and packaging the resulting aqueous suspension concentrate composition. x f; :a 15 18. A method according to Claim 17, wherein said secondary pesticide(s) is water soluble or has a melting point greater than 70 0 C. 19. A method according to Claim 18 or Claim 19, wherein said orange crystal form is 10% orange crystal form to 90% yellow crystal form to 100% orange crystal form. A method according to any one of Claims 17 to 19, wherein said suspended particle size is 2 microns to 10 microns. 21. A method according to Claim 18, said composition comprising, on a weight to volume basis: about 5.0% to 50.0% pendimethalin; about 0% to
50.0% said second higher melting or water soluble pesticide; about 2.0% to 20.0% of the surfactants cresol-formaldehyde condensates and sulfonates thereof, napthalene formaldehyde condensates and sulfonates thereof, j lignosulfonates, and mixtures thereof; about 0.05% to 2.5% of the suspending agent Xanthan gum, guar gum, gum arabic, or cellulos derivatives; about 2.0% to 15,0% of the antifreezing agents ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming agent; O about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and water to total said composition to 100%. 22. An aqueous suspension concentrate composition of pendimethalin, substantially as hereinbefore described with reference to any one of the Examples. 23. A method for the preparation of an aqueous suspension concentrate composition of pendimethalin, substantially as hereinbefore described with reference to any one of the Examples. DATED this FIFTH day of DECEMBER 1989 American Cyanamid Company Patent Attorneys for the Applicant SPRUSON FERGUSON Mr 8u."
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| US86686486A | 1986-05-23 | 1986-05-23 | |
| US867106 | 1986-05-23 |
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| CA1289065C (en) * | 1986-05-23 | 1991-09-17 | Leonard John Morgan | Aqueous suspension concentrate compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163598A1 (en) * | 1984-04-27 | 1985-12-04 | Ciba-Geigy Ag | Herbicidal compositions |
| AU7335687A (en) * | 1986-05-23 | 1987-11-26 | American Cyanamid Company | Aqueous suspension concentrate compositions |
| AU7330887A (en) * | 1986-05-23 | 1987-11-26 | American Cyanamid Company | Stable aqueous suspension concentrate compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163598A1 (en) * | 1984-04-27 | 1985-12-04 | Ciba-Geigy Ag | Herbicidal compositions |
| AU7335687A (en) * | 1986-05-23 | 1987-11-26 | American Cyanamid Company | Aqueous suspension concentrate compositions |
| AU7330887A (en) * | 1986-05-23 | 1987-11-26 | American Cyanamid Company | Stable aqueous suspension concentrate compositions |
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|---|---|
| AU7335787A (en) | 1987-11-26 |
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