IL33113A - Surface active agents employed to enhance the effect of herbicides - Google Patents
Surface active agents employed to enhance the effect of herbicidesInfo
- Publication number
- IL33113A IL33113A IL33113A IL3311369A IL33113A IL 33113 A IL33113 A IL 33113A IL 33113 A IL33113 A IL 33113A IL 3311369 A IL3311369 A IL 3311369A IL 33113 A IL33113 A IL 33113A
- Authority
- IL
- Israel
- Prior art keywords
- siloxane
- formula
- value
- inclusive
- ch2ch20
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 30
- 239000004094 surface-active agent Substances 0.000 title description 18
- 230000000694 effects Effects 0.000 title description 6
- 241000196324 Embryophyta Species 0.000 claims description 29
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 25
- 230000002363 herbicidal effect Effects 0.000 claims description 24
- -1 halogenated hydrocarbon radical Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 3
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- JODDYISEVBVLSB-UHFFFAOYSA-N 2-chloro-n-phenyl-n-propylacetamide Chemical compound CCCN(C(=O)CCl)C1=CC=CC=C1 JODDYISEVBVLSB-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229950004243 cacodylic acid Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910003946 H3Si Inorganic materials 0.000 description 1
- 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Surface active agents employed to enhance the effect of herbicides
DOW COROT& CORPORATION
0.-31388
This invention relates to a method for enhancing the effect of herbicides.
Herbicides are employed in a wide variety of situations, for example for the purpose of con-trolling weeds. For example, 2-chloro- -ethylamino-6-isopropylamino-l,3 , 5-triazine (sold as "Atrazine"), which is a commercially available herbicide, is commonly employed as a killer of the weeds which may be detrimental to com crops. Accordingly, it is an object of the present invention to enhance the effectiveness of the Atrazine (as well as other well-known herbicides) by incorporating therein certain siloxanes as surface active agents. The use of the siloxane surface active agents potentiate the desired herbi-cidal activity, i.e. the effect is far more rapid and a greater degree of weed control is exhibited.
These and other attendant objects will become apparent from the follovdng detailed description of the invention.
This invention therefore relates to a method for enhancing the effectiveness of herbicide solutions by incorporating therein 0.1 percent to 2.0 percent, based upon the final volume of the herbicide solution, of a certain surface active agent, said certain sur-face active agent being either
(A) A siloxane of the formula:
0 0
II It
H3Si(0SiR2)x(0SiR/~R'0(R"0)2CR"' (COA )w_7)y0SiR3
in which
R is a monovalent hydrocarbon or a halogenated hydrocarbon radical free of aliphatic unsat- uration containing from 1 to 6 carbon atoms inclusive,
R' is a divalent hydrocarbon radical containing from 1 to 12 carbon atoms inclusive,
R" is a divalent hydrocarbon radical free of
aliphatic unsaturation containing from 2 to
carbon atoms inclusive,
R"' is a divalent or trivalent hydrocarbon
radical containing from 2 to 6 carbon atoms inclusive,
A is a hydrogen atom, an amino group of the
formula +HN=, in which the three valences
of the N atom are satisfied with any monovalent or any polyvalent hydrocarbon or hydrocarbon ether radical. In other words, A
can be the H of a carboxyl group or the
anion of an ammonium salt, an amine salt or an alkali or alkaline earth metal salt, and an alkali or alkaline earth metal,
x has a value of from 0 to 100 inclusive, y_ has a value of from 1 to 100 inclusive,
z has a value of from 1 to 50 inclusive, and w . is 1 or; 2; or
a siloxane of the formula:
R' 3Si(0SiR2 )x( OSiRfR'O (CH2CH20 ) bH_ OSi
wherein R, R' , x and y_ are as above defined and
b has, a value of from # to 16 inclusive.
As noted in the formulae defined above, R can be any monovalent and halogenated monovalent
hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms such as the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, hexyl, phenyl, 3,3,3-Orifluoropropyl, chloro- ' methyl, bromomethyl, broraopropyl, gamma-chloropropyl and the iodophenyl radical. For purposes of the
, present invention, it is preferred that the R radical be methyl .
Although R' is preferably propylene, it
can be any divalent hydrocarbon radical containing from 1 to 12 carbon atoms such as the methylene,
ethylene, propylene, butylene, isobutylene, hexylene, decylene, octadecylene , phenylene, methylphenylene , vinylene and the allylene radical.
R" can be a divalent hydrocarbon radical containing from 2 to carbon atoms inclusive, i.e.
the ethylene (preferred), propylene and the butylene radical .
divalent or
R" can be a/trivalent hydrocarbon radical containing from 2 to 6 carbon atoms' such as the hexylene, methylene, ethylene, propylene, the -CHCHg-,
1 t
-CH2CHCH2-, -CH2 A—
the -CH2CH2CH2CH2CHCH2- radical. For purposes of this invention, ethylene is to be preferred.
A is a hydrogen atom or an alkali metal or alkaline earth metal such as sodium, lithium, potassium, cesium, magnesium, calcium or strontium.
Also A can be an anion derived from ammonia, quaternary ammonium hydroxides such as (CH^J^NOH,
(CH^C^l^yNOH or (CH ^C^NOH or amines such
as ( NVNH2, morpholine, (CH3)2NH, (Ci^Ci^^N,
pyridine,
As noted above, x has a value of from 0
to 100 inclusive, y_ has a value of from 1 to 100
inclusive, z has a value of from 1 to 50 inclusive, w has a value of from 2 to 6 inclusive, and b has a value of from 3 to 16 inclusive..
... Examples of the siloxanes (A) for use in the invention are:
(CH3)3Si(OSi/'"CH3_2)3(OSiCH3/(CH2.)30(CH2CH20)12- . 0 0
tt tt
CCH2CH2C0H_7)0Si(CH3)3 ,
0 0
tt It
(Cl^^SiOSiCl^ (CI^^OtC^CI^Ol-^CC^iCOH) 2J-
0 0
tt It
CH2)30(CH2CH20)12CCH2CH2C0H
_7'-
The siloxanes (A) ' including those specified above are readily prepared by merely adding an
organosilicon compound of the formula:
R2 R
t t
R3S OSi)x 0S yOSiR3
R»
t .
0-(R»0)zH
in which R, R' , R" , x> ∑ a d z are as above defined to any cyclic anhydride of a carboxylic acid (e.g. succinic anhydride, dodecenyl succinic anhydride, glutaric anhydride, phthalic anhydride, maleic
anhydride and tri ellitic anhydride), heating the admixture (about SO°C or above) in either the presence or absence of a suitable catalyst, and ultimately recovering the desired siloxane (A). To obtain the corresponding salt, a stoichiometric amount of the-amine or the appropriate alkali metal or alkaline earth metal is simply added to the recovered siloxane (A) at room temperature. In the latter case, the siloxane polymer and/or amine or appropriate alkali metal or alkaline earth metal are preferably diluted in a suitable organic solvent, for example an alcohol such as methanol.
The siloxanes (B) are commercially available materials and are well known in the art. The siloxanes (B) are prepared by the well known process of adding a terminally unsaturated polyoxyethylene
glycol to the appropriate Si-H containing siloxane mixture in the presence of a suitable catalyst such as chloroplatinic acid. The preparation is illustrated by the following equation:
xi3SiO(i.SiO xSiH3 + CH2=CH(H» )0(E"0)2H
H
R
E'0(R"0)2H
in which R, R* and R" are as defined above.
Known herbicides whose effectiveness can be substantially increased by using the siloxanes (A) or (B) as surface active agents include methanear-senic acid, dimethylarsenic acid, 1,1* -dimethyl-4,4' -bipyridinium, 2, 2-dichloropropionic acid, 4,6-dinitro-o-sec-butylphenol, N' (3,4-dichlorophenyl)N,N-dimethyl urea, 2, 4-D ( , 4-dichlorophenoxyacetic acid) , 2-chloro-N-propylacetanilide, 3-amino-2, 5-dichlorobenzoic acid, 2, 6-dinitro-N,N-dipropyl-4-trifluoromethylantline,
3-amino-l, 2, 4-triazole and 2-chloro-4-ethylamino-6-isopropylamino-1,3, 5-triazine among numerous others.
The herbicides noted above are principally employed as weed killers, for example to destroy weeds whichhinder the growth of feed or forage crops such as corn, sorghum, soybeans, wheat and sugar beets.
This invention also relates to a method for inhibiting the growth of weeds by applying thereto an
effective amount of a herbicide having incorporated therein from 0.1 percent to 2.0 percent based upon the final volume of the herbicide solution of a
certain surface active agent, said certain surface active agent being selected from the group consisting of a siloxane (A) and (B).
In practice, the herbicide is normally dissolved in a suitable liquid such as water, an alcohol, ether or ketone. The siloxane (A) or (B) is then added in an amount of from 1.0 percent to
50.0 percent by weight (preferably 30.0 to 40.0
percent by weight ) , based upon the weight of the herbicide solution. The above mixture is then diluted in a suitable carrier, for example water, kerosene, or a non-phytotoxic solvent such as agricultural spray oil. Dilution is in an amount of from 10-fold to 100-fold and preferably about 50-fold. The finished formulation is then applied to the pertinent plant in accordance with good agricultural practice (band-spray, directed spray, broadcase spray and soil incorporation spray) .
Alternatively (and the preferred method) is to take a commercially formulated herbicide such as 2, -D which has been diluted and prepared for immediate application. To this formulated product, the siloxane (A) or. (B) is added as an adjuvant substance in an amount of 0.1 percent to 2.0 percent of the final volume . The finished material is then sprayed by known agricultural methods such as noted above.
The following examples illustrate the invention.
Example 1
A hybrid corn was planted on three (3) separate plots (6' x 22') of moist soil. Three (3) rows of corn were planted per plot at intervals of approximately one foot. A siloxane of the formula:
t '
(CH3.)3Sii-OSi^1_gOSi(CH3 )3
(CH2)3-O(CH20H2O)12H
was added as an adjuvant substance in amounts of 0, 0.5, 1.0 and 2.0 percent of the final volume to 2-chloro-4-ethylamino-6-isopropylamino-l,3 , -triazine . Each plot was then sprayed (post-emergence application) at an application rate of 30.0 and 40.0 gallons per acre. Each of the three plots were then averaged and the Table . I indicates the results obtained with respect to weed kill and initial weed coverage.
In Table I,, the following rating system applies:
Weed Control Response
Rating
Number % Weed Control
1 No apparent effect 0 - 10$
2 Very poor 10 - 20%
3 Poor 20 - 30
Fair 40 - 50
6 Fair- good 50 - 60%
7 Good 60 - 70%
8 Good - very good 70 - B0
9 Very good - excellent SO - 90%
Excellent 90 - 100%
Initial Weed Coverage on Com Test Plots
L - Light weed coverage, less than 2 inches average
height, 0 - 30$ weed cover
M - Moderate weed coverage, 2 to 4 inches average
height, 30 - 60% weed cover
H - Heavy weed coverage, 4 inches and above height,
60 - - 99% weed cover
In the above example, it is to be noted that the use of no surfactant resulted in no enhancement of the effect of the herbicide in destroying weeds, however, when the siloxane surfactant was added, weed kill was substantially increased particularly when the application rate was also increased.
Example 2
Hybrid corn was planted in S-gallon
containers (6 plants per container). Weed-seed was planted with the corn and sown to provide
significant weed growth. A siloxane of the formula:
(CH3)3Si OSi 1_gOSi(CH3)3
(CH2)30(CH2CH20)12H
was added as an adjuvant substance in amounts of
0.25, 0.50 and 1.0 percent of the final volume to
2-chloro- -ethylamino-6-isopropyl-amino-l, 3·, 5-triazine. Each container was then sprayed (post-emergence application) at an application rate of 30.0 gallons per acre. Visual observations were conducted daily over an extended period of time and an indication with respect to weed kill and initial weed coverage was obtained. The above evaluation was made employing a control containing no Atrazine and no adjuvant substance and also with a control
treated with Atrazine at 2.0 pounds per acre but containing no adjuvant substance.
In contrast to the controls, all of the containers treated with the concentrations of the adjuvant substance and the herbicide clearly indicated surfactant qualities (it was a surface active agent) and it did. increase or. potentiate the herbi-cidal activity of the herbicide as compared to the
Example 3
When the following herbicides were substituted for the Atrazine of Example 1 and applied in accordance with the procedures of Example 1, substantially equivalent results were obtained:
(A) DSMA (methanearsenic acid),
(B) Caco (dimethylarsenic acid),
(C) Paraquat
-bipyridinium) ,
(D) Dalapon ( 2, 2-dichloropropionic acid),
(E) D BP ( ,6-dinitro-o-sec-butylphenol) ,
(F) Diuron ~N' (3, -dichlorophenyl)N,N-dimethyl
(G) 2,4-D ( 2, -dichlorophenoxyacetic acid),
(H) Ramrod ( 2-chloro-N-propylacetanilide ) ,
(I) Amiben (3-amino-2, 5-dichlorobenzoic acid),
(J) Treflan ( 2, 6-dinitro-N,N-dipropyl-4-trifluoro- methylanaline ) ,
(K) Amitrole (3-amino-l, 2, 4-triazole ) .
Table I
Application
Pounds of Rating Initial Rate Herbicide Weed Weed (Gallons per
Per Acre % Surfactant Kill Coverage Acre)
2 0 3 H 30
2 0 5 L 40
2 1/2 4 H 30
2 1 5 M 30
2 1 9 • L 40
2 2 M 30
2 2 . 9 M 40
3 0 3 H 30
3 0 5 M 40
3 1/2 4 M 30
3 1 6 L 30
3 1 8 H 40
3 2 6 L 30
" " 3' 2 7 M 40
4 0 3 L 30
4 0 6 M 40
4 1 a M 30
4 1 9 L 40
4 2 L 30
4 2 9 L 40 o herbicide, no surfactant None M None
(Control)
I
Example 4
Weed seed was sown to totally cover four separate plots (6ft x 22ft) of moist soil.
Three of these plots were sprayed, (post-emergence application), at an application rate of 40 gallons per acre of the recommended dilution of the herbicide 2,2-dichloropropionlc acid to which was added an (A) type slloxane surface active agent of the formula:
CH,
(0H3)3Si(-O-Sri-)n0-Si (CH3)3
as an adjuvant substance in the amounts of 0.25, 0.50 and 1.0 per cent of the final dilution volume of the herbicide.
One plot, ' (control) , was sprayed (post-emergence application) at the application rate of 40 gallons per acre of the diluted herbicide 2 , 2-dichloro-propionic acid without the surface active agent type (A) slloxane present,
1
The four plots were observed and the results obtained with respect to initial weed-coverage and final weed-kill are shown below:
Pounds of + Initial* Appl. Rate
Herbicide $> Rating Weed . (Gallons per
Per Acre Surfactant Weed Kill Coverage Acre)
0 3 H 40
0.25 3 H 40
0.50 4 H 40
1.00 4 H 40
■f- ss Ratings correspond to the system shown on page 10, lines 1-22 of the specification.
Claims (11)
1. A method for enhancing the eff ectiveness of herbicide solutions by incorporating therein from 0.1 percent to 2.0 percent , based upon the final volume of the herbi cide solution, of (A ) a siloxane of the formula: R Ά R1 0 0 t n tt O i ^'O LCR"' ( C0A )i r • in which R is a monoval ent hydrocarbon or halogenated hydrocarbon radical free of aliphatic unsaturation containing from 1 to 6 carbon atoms inclusive , ft' is a divalent hydrocarbon radical containing from 1 to 12 carbon atoms inclusive , R" is a divalent hydrocarbon radical free of aliphatic unsaturation containin from 2 to 4 carbon atoms inclusive , R,M is a divalent or trivalent hydrocarbon radical containing from 2 to 6 carbon atoms inclusive , A .: is a hydrogen atom, an amino group or an alkali or alkaline earth metal , x has a value of from 0 to 100 inclusive, y_ has a value of from 1 to 100 inclusive, z has a value of from 1 to 50 inclusive, and or w has a value of from 1 to 2 inclusive; a» -(B) a siloxane of the formula: RjSi OSi)x4-OSi)-yOSiR3 R' t . 0(CH2CH20)bH in which R, Rf , x and y_ are as defined above ■ and b has a value of from & to 16 inclusive.
2. A method as claimed. in claim 1 in which R is a methyl radical, R' is a propylene radical, R" is an ethylene radical, Rm is an ethylene radical, A is a hydrogen atom, x has a value of from 0 to 50, y_ has a value of from 1 to 100, z has a value of from 1 to 20 and w has a value of from 1 to 2.
3. A method as claimed in claim 1 in which the siloxane (A) is of the formula: , (CH3)2 CH3 (CH2), 0 0 t * J It tt 0(CH2CH20)12CCH2CH2C0H
4. A method as claimed in claim 1 in which the siloxane (A) is of the formula: (CH3)3Si-0-Si-0-Si(CH3)3 0-(CH2CH20) 12CC6H3 ^G0H ^ 2
5. A method as claimed in claim 1 in which the siloxane (A) is. of the formula: (CH3 )3Si-0-Si-0-Si(CH3 )3 (CH )~ 0 0 t it it 0-(CH2CH20) 12CCH2CH2C0H
6. A method as claimed in claim 1 in which the siloxane (A) is of the formula: (CH-)_Si^0Si)„ 0Si^0Si(CH. ) y I t y (CHp) 0 0 t Λ y it it 0-(CH2CH20)12CCH2CH2C0H
7. A method as claimed in claim 1 in which the siloxane (A) is of the formula: (CH3)3Si-OSi^2OSi(CH3)3 CH 0 0
8. A method as claimed in claim 1 in which the siloxane (B) is of the formula: (CH^ )3SHOSi|2OSi ( CH3 ) 3 (CH2)3 0 ( CH2CH20 ) 12H
9 . method as claimed in claim 1 in which the siloxane (3) is of the formula: (CH3 ) 3Si-O 3i (CH3 )3
10 . A method of controlling or destroying weeds which comprises applying to the weeds an improved herbicide solution produced by the method as claimed in any of the preceding claims.
11 . An improved herbicide solution comprising a known herbicide and from 0 .1 to 0 . 2 percent, based on the final volume of the solution, of a siloxane (A) as defined in claim 1 or a siloxane (B) as defined in claim 1 .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76698368A | 1968-10-11 | 1968-10-11 | |
| US81806069A | 1969-04-21 | 1969-04-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33113A0 IL33113A0 (en) | 1969-12-31 |
| IL33113A true IL33113A (en) | 1973-04-30 |
Family
ID=27117834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33113A IL33113A (en) | 1968-10-11 | 1969-10-03 | Surface active agents employed to enhance the effect of herbicides |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT300451B (en) |
| BE (1) | BE740113A (en) |
| CH (1) | CH533945A (en) |
| DE (1) | DE1950380A1 (en) |
| FR (1) | FR2020409A1 (en) |
| GB (1) | GB1255249A (en) |
| IL (1) | IL33113A (en) |
| NL (1) | NL6915346A (en) |
| PH (1) | PH9322A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247050A1 (en) * | 1982-12-20 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | HERBICIDAL AGENTS |
| HUT55189A (en) * | 1988-06-14 | 1991-05-28 | Monsanto Co | Herbicidal composition with improved effect and comprising wetting agent and silicone surface active material |
| US5017216A (en) * | 1988-08-15 | 1991-05-21 | Dow Corning Corporation | Postemergent herbicide compositions containing silicone glycol adjuvants |
| CA1337459C (en) * | 1988-08-15 | 1995-10-31 | Lenin J. Petroff | Postemergent herbicide compositions containing silicone glycol adjuvants |
| US5145978A (en) * | 1988-08-15 | 1992-09-08 | Dow Corning Corporation | Postemergent herbicide compositions containing silicone glycol adjuvants |
| US4990175A (en) * | 1989-06-13 | 1991-02-05 | Dow Corning Corporation | Foliar applied herbicidal compositions containing a silicone glycolsilicone alkane terpolymer adjuvant |
| US4933002A (en) * | 1989-11-21 | 1990-06-12 | Dow Corning Corporation | Postemergent herbicide compositions containing acetoxy-terminated silicone glycol and dispersant |
| US5145977A (en) * | 1989-11-21 | 1992-09-08 | Dow Corning Corporation | Postemergent herbicide compositions containing acetoxy-terminated silicone glycol and dispersant |
| US5059704A (en) * | 1989-12-13 | 1991-10-22 | Dow Corning Corporation | Foliar-applied herbicidal compositions containing a silicone glycol-silicone alkane terpolymer adjuvant |
| JP3705954B2 (en) * | 1999-05-19 | 2005-10-12 | 信越化学工業株式会社 | Agrochemical spreading agent |
| US6734141B2 (en) | 2001-11-21 | 2004-05-11 | Goldschmidt Ag | Use of non-spreading silicone surfactants in agrochemical compositions |
-
1969
- 1969-10-01 GB GB48159/69A patent/GB1255249A/en not_active Expired
- 1969-10-03 IL IL33113A patent/IL33113A/en unknown
- 1969-10-06 DE DE19691950380 patent/DE1950380A1/en active Pending
- 1969-10-07 AT AT944269A patent/AT300451B/en not_active IP Right Cessation
- 1969-10-10 NL NL6915346A patent/NL6915346A/xx unknown
- 1969-10-10 BE BE740113D patent/BE740113A/xx unknown
- 1969-10-10 PH PH10788*UA patent/PH9322A/en unknown
- 1969-10-10 CH CH1528069A patent/CH533945A/en not_active IP Right Cessation
- 1969-10-10 FR FR6934717A patent/FR2020409A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL6915346A (en) | 1970-04-14 |
| FR2020409A1 (en) | 1970-07-10 |
| PH9322A (en) | 1975-09-17 |
| CH533945A (en) | 1973-02-28 |
| BE740113A (en) | 1970-04-10 |
| IL33113A0 (en) | 1969-12-31 |
| DE1950380A1 (en) | 1970-04-23 |
| AT300451B (en) | 1972-07-25 |
| GB1255249A (en) | 1971-12-01 |
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