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CA1208929A - Concentrated basal spray - Google Patents

Concentrated basal spray

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Publication number
CA1208929A
CA1208929A CA000440944A CA440944A CA1208929A CA 1208929 A CA1208929 A CA 1208929A CA 000440944 A CA000440944 A CA 000440944A CA 440944 A CA440944 A CA 440944A CA 1208929 A CA1208929 A CA 1208929A
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CA
Canada
Prior art keywords
phosphate
acid
aryl
alkyl
group
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
Application number
CA000440944A
Other languages
French (fr)
Inventor
Roy R. Johnson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Application granted granted Critical
Publication of CA1208929A publication Critical patent/CA1208929A/en
Expired legal-status Critical Current

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Abstract

ABSTRACT
This invention relates to the discovery that esters of phosphoric and phthalic acids are effective wood penetrant-carriers for biocidally active ingredients, especially oil soluble or oil miscible ingredients, in basal sprays.

Description

~o~æ~

CONCENTRATED BASAL SPRAY
Field of the Invention This invention relates to the use of phosphoric and/or phthalic acid esters as wood penetrants for biocidally active ingredients in basal spray compositions.
Background of the Invention The ability to control undesirable woody plants or undesirable fungus or pests in woody plants by individual stem applications of herbicides; plant growth regulators; fungicides; and insectici~as rather than by broadcast foliar sprays i~ highly desirable from both economic and environmental consi~erations. Today, for example, controlling undesirable woody plants by individual stem applications of herbicides is an important tool ~or the effective management of woody vegetation on highway, public utility, railroad rights-of-way, and similar areas.
The application of high volume, oil miscible herbicide sprays diluted with fuel oil, kerosene, or other petroleum solvents has been the primary metbod of individual stem brush control since phenoxy herbicides were developed in the 1940's~ However, recent increases in the cost of petroleum solvents have made this technique, called basal spraying, uneconomical.
Soil active herbicides, water/oil mixtures, and cut stem injection techniques suGh as frilling have been utilized in an attempt to find a replacement ~or the original high-volume oil, basal spray technique. All of these replacement techniques will afford some control of many woody
2~

plants, but they are subject to disadvantages such as high cost; injury to off-target vegetation from root uptake; limited use at below freezing temperatures; and the necessary use of sharp, dangerous tools to cut the woody plant stems.
It would be highly desirable to have a technique for r~alizing control of woody plants and unde~ira~le organisms that infest said plants that obviated the afore-mentioned disadvantages, e.g., a low cost, low volume, injury specific application technique that could be u~ilized in any season without the use of dangerously sharp instruments.
SUMMAR~ OF TH13 I~IVENTION
This invention relates to the discovery.
15. that esters of phosphoric and phthalic acid~ are effective wood penetrant-carriers or fungicides, insesticides, herbicides, and plant growth regulators. The aforementioned penPtrant-carriers are especially ef~ective when the active ingredients are oil-soluble and/or oil miscible. Basal spray compositions using these penet.rants can be effectively uRed a) with 1/10 of the total conventional volume - thus eliminating the necessity o~ transporting large volumes of expensive fuel oil to the use site; b) in any season - the absence of water eliminates freezing problems; and c) with herbicides o limited soil activity thus eliminating or significantly reducing potential injury to off-target vegetation.
~ETAILED DESCRIPTIO~ OF THE INVENTION
This invention relates to compositions comprising a penetrant-carrier in combination with a ~-13722 æ~

herbicide, plant growth .regulator, fungicide, or insecticide, all the aforementioned hereinafter generically referred to as biocides, and the use of this composition in a basal spray to control woody plants, regulate the growth of said plants or control organisms which infest said plants.
The term "basal spray" means that the composition is applied usually via conventional low volume spray apparatus, to the stem or bark of a woody plant, usually a~ the ba~al portion of the plant. Generally, the composition is sprayed onto from about a 12 to 36 inch portion of the lower end of the ~tem, i.e., that end of the st~m closest to the ground or trunk.
The penetrants of this invention are a) compounds o~ phosphorous having the formula:
/Xl~l ()n = P X2R2 ~X3R3 wherein xl, x2 and X3 are individually O or S;
n is 0 ~r l;
R1 is selected from the group consi~ting of hydrogen, Cl to ClO alkyl, aryl, aryl-~Cl-cl0) alkyl, cycloaliph 2~ and heterocyclic; and R2 and R3 are individually selec~ed from the group consisting o~ Cl-ClO
alkyl, aryl, aryl-(C~-C10) alkyl, cycloaliphatic~ and heterocyclic.
In other words, at least two of the groups attached to the oxygens/sulfurs connected by a ~zo~æ~

single bond to the phosphorous group are organic groups, while the other is e.ither an organic group or hydrogen.
~) esters of phthalic acid having the formula C O - R

wherein Rl,and R2 are individually selected from the group consistlng of hydrogen, Cl-ClO
alkyl, aryl. and aryl-(C1-ClO)alkyl with the proviso that Rl and R2 cannot both be hydrogen, c) and combinations of the a~ove-described phosphoric and phthalic acid esters.
The preferred penetrant-carriers are the following:
symmetrical triaryl phosphate esters such as triphenyl phosphate;
tricresyl phosphate (all isomers); and tri(O-cresyl) phosphate, unsymmetrical triaryl phosphate esters such as cresyl diphenyl phosphate ester;
alkyl diaryl phosphate esters such as 2-ethylhexyl diphenyl phosphate;
dialkyl phosphate esters such as dibutyl phosphate;

~208~

trialkyl phosphate esters such as tributyl phosphate;
trldecyl phosphate' triethyl phosphate; and tri(2-ethylhexyl~ phosphate:
trialkyl phosphorotrithioate esters such as S,S,S, tributylphosphorotrithioate trialkyl phosphorotrithioite esters such as tributyl phosphorotrithioite;
mono- and di-alkyl phthalate e~ters such as dibutyl phthalate; and dioctyl phthalate.
The most preferred penetrant-carrier of this invention is tributyl phosphate Although the effectiveness in basal sprays of most herbicide~, fungicides, insectici~es an~
plan growth regulators can be enhanced via the u~ilization of the penetrant-carriers of this invention, the preferred active ingredients are oil soluble or oil miscible.
~he preferred active ingredients of this invention are, for example, herbicides which are phenoxy acids and e~ters such as:
2,4-dichlorophenoxypropionic acid, butoxy-ethanol ester, 2,4-dichlorophenoxyacetic acid, butoxy-ethanol ester.
2,4,5-trichlorophenoxyacetic acid, butoxy-ethanol ester, 2-(2,4,5~trichlorophenoxy)propionic acid, 4-(2,4-dichlorophenoxy)butyric acid, 4-chloro-l~methylphenoxyacetic acid, 4-(2-methyl-4-chlorophenoxy)butyric acid, and 2-(4-chloro-2-methylphenoxy)propionic acid.

32~

-- 6 ~

Other preferred herbicides include 4-amino-3,5,6-trichloropicolinic acid, 2-methoxy-3,6-dichlorobenzoic acid~ and
3~5,6-trichloro-2-pyridinyloxyacetic acid.
Combinations of the above with themselves or with other active ingredients can also be desirable since two or more of the effective, i,eO
active, ingredien~s can be used in combination to incr~ase the number of species of woody plants or plant pests which can be controlled.
This invention utilizes an amount of active biocide equivalent to that used in a conventional basal or stump spray for control o~ woody plants or plant pests but uses a significantly lower volume of penetrant-carrier or combination of carriers in lieu of the conventional larger volume of fuel oil or kerosene.
Whereas a conventional basal herbicidal spray would apply from 30 to 100 gallons per acre of a herbicide/oil mixture containing about 1 to 20, preferably about 5 to about 16 pounds o~ a phenoxy herbicide, with the instant invention only from about 1 to about 15, pre~rably fro~ about 3 to lO
total gallons containing the same amount of active 2S herbicide would be applied per acre. Usually the preferred amount o~ spray volume needed is about l/lOth the amount of actiYe oil-carrier spray volume conventionally used.
A solvent diluent is preferably mixed with the active~penetrant combinations to solubilize the active and obtain desired active concentration for good spray distribution, iOe, good dispersion with conventional equipment~

~-13722 2~

Although many organic diluents would suffice - the choice being usually governed by economics - the preferred solubili2lng diluents consist o~ about 90 percent naphthenic oil with the balance being kerosene.
The ratio of biocidally active ingredient to the penetran~ should range from a minimum of about 1030 to a maximum of about 20:1, preferably from about 1:10 to about 2:1 and most preferably ~0 from about 1:1.5 to about 1.~
The solvent diluent is present in the basal concentrate at a ratio of solvent diluent to active biocidal ingredient at from about 0 to about 25, preferably from about 0~2 to about 10 and most prefera~ly from about 0~5 to about 4 time~ the active ingredient~
The following examples are set forth for purposes of illustration so that those skilled in the art may better understand the invention, and it should be understood that they are not ~o be construed as limiting this invention in any manner.
EXAMPLE I
The compositions of the basal concentrate sprays used in this and the following examples are ~5 as ~ollows:
Composition A:
Ingredient Percent By Weight 2~4-dichlorophenoxyacetic acid, butoxyethanol ester 12.41 3~ 2-4-dichlorophenoxypropionic acid~
butyoxyethanol ester 120 99 tributyl phosphate 24.62 ` D-13722 -~2~ 2~

naphthenic oil/kerosene solvent diluent _9.98 TOTAL100~00 Composition B:
Ingredient Percent sy ~eight 2,4,5-trichlorophenoxyacetic acid, butoxy ~thanol ester22.82 tributylphosphate 24.50 naphthenic oil/kerosene solven~
diluent 52.68 T05~L 100.00 Composition C:
Ingredient Percent By Weight 2,4-dichlorophenoxyacetic acid, butoxyethanol ester 9.25 2,4-dichlorophenoxypropionic acid butoxyethanol ester 9.25 3,5/6-trichloro-2-pyridinyloxyacetic acid ~7.16 tributylphosphate 18.52 naphthenic oil/kerosene solvent diluent 45.82 TO~AL

Composition D:
Ingredient Percent By Weight 2,4-dichlorophenoxyacetic acid, butoxyethanol ester 9.31 2,4-dichlorophenoxypropionic acid butoxyethanol ester 9.31 ~z~
4-amino-3,5,6-trichloropicolinic acid 9.25 tributylphosphate 18~60 naphthenic oil/kerosene solvent diluent 53.53 TOTAL

Control: Weedone 170TM a woody plant herbicide sold by Union Carbide.*
IngredientPercent By Weight 2,4-dichlorophenoxypropionic acid butoxyethanol es~er 2~.3 2,4-dichlorpheoxyacetic acid butoxyethanol ester 29.9 inert ingredients 40.8 TOTAL 100.0 *Applied as a mixture of abou 3 to 4 gallons in 100 gallons of oil as recommended.
~he above-identified compositions were applied as a basal spray using conventional equipment to various trees in the spring (3une) in Pennsylvania and Maryland with the following results:

- 10 - ~.2~ 29l PERCENT CONTROL*
Red A. W. R.
Composition maple elm Persimmon ash Sycamore oak Pine Spruce 100 100 10~100 10~ 100 100 100 Control 70 10U 10080 100 90 70 60 *Evaluation was based on the amount of live growth remaining above the ground ~2198~332~

EXA~PLE II
The following basal spray field trials were conducted in May in New York State with evaluations in August of the 6ame year~ A11 trials were with Composition C~
SPECIES .PERCENI~ CONTROL
white ash 98 hickory 90 white pine 98 0 pin cherxy 100 northern red oak 80 white oak 100 red maple 100 aspen 10 0 ~5 black locust 97 white birch 98 EXA~PLE III
The following basal spray field trials were conducted in the spring and summer months in Virginia.
SPECIES PERCENT CO~TROL
Comp. AComp. C
white oak 98 100 red oak 98 87 tulip-poplar lQ0 100 ch~stnut oak 95 100 Sassaf ras 10 0 10 0 hickory 100 100 sourwood 42 100 red maple 100 --black cherry 80 90 z~
~ 12 --SPECIES PERCENT CONTROL
Comp. AComp. C
black locust 10û 100 black gum 100 --sumac 100 --pe r s immon 9 Q - -Ailanthus 100 100

Claims (32)

WHAT IS CLAIMED IS:
1. A method of controlling undesirable plants or plant pest organisms which comprises basally spraying said plants or organism-containing plants with a mixture comprising:
(a) a biocidally active ingredient;
and (b) a penetrant-carrier comprising a compound selected from the group consisting of (1) compounds of the formula wherein X1, X2 and X3 are individually O
or S;
n is 0 or 1;
R1 is selected from the group consisting of hydrogen, C1 to C10 alkyl, aryl, aryl-(C1-C10)alkyl, cycloaliphatic and heterocyclic; and R2 and R3 are individually selected from the group consisting of C1-C10 alkyl, aryl, aryl-(C1-C10)alkyl, cycloaliphatic, and heterocyclic;
(2) compounds having the formula wherein R1 and R2 are individually selected from the group consisting of hydrogen, C1-C10 alkyl, aryl, and aryl-(C1-C10)alkyl with the proviso that R1 and R2 cannot both be hydrogen; and (3) combinations thereof.
2. The method of claim 1 wherein said biocidally active ingredient is a herbicide.
3. The method of claim 1 wherein said biocidally active ingredient is a fungicide.
4. The method of claim 1 wherein said biocidally active ingredient is a plant growth regulator.
5. The method of claim 1 wherein said biocidally active ingredient is an insecticide.
60 The method of claim 1 wherein said penetrant-carrier comprises a compound selected from the group consisting of triphenyl phosphate;
tricresyl phosphate; cresyl diphenyl phosphate;
2-ethylhexyl diphenyl phosphate; dibutyl phosphate;

tributyl phosphate; tridecyl phosphate; triethyl phosphate; tri(2-ethylhexyl) phosphate;
S,S,S,-tributylphosphorotrithioate; tributyl phosphorotrithioite; dibutyl phthalate; and dioctyl phthalate.
7. The method of claim 1 wherein said penetrant-carrier is tributyl phosphate.
8. The method of claim 1 wherein said biocidally active ingredient is oil soluble or oil miscible.
9. The method of claim 1 wherein said mixture additionally contains an organic solvent diluent.
10. The method of claim 9 wherein said diluent comprises naphthenic oil.
11. The method of claim 1 wherein the ratio of said biocidally active ingredient to said penetrant-carrier is from about 1:30 to about 20:1.
12. The method of claim 11 wherein said ratio is from about 1:10 to about 2:1.
13. The method of claim 11 wherein said ratio is from about 1:1.5 to about 1.5:1.
14. The method of claim 9 wherein the ratio of said diluent to said biocidally active ingredient is from about 0 to about 25.
15. The method of claim 14 wherein said ratio is from about 0.2 to about 10.
16. The method of claim 14 wherein said ratio is from about 0.5 to about 4.
17. A method of controlling undesirable plants which comprises basally spraying said plants with a mixture comprising:
(a) a herbicide; and (b) a penetrant-carrier comprising a compound selected from the group consisting of (1) compounds of the formula wherein X1, X2 and X3 are individually O
or S;
n is 0 or 1;
R1 is selected from the group consisting of hydrogen, C1 to C10 alkyl, aryl, aryl-(C1-C10)alkyl, cycloaliphatic and heterocyclic; and R2 and R3 are individually selected from the group consisting of C1-C10 alkyl, aryl, aryl-(C1-C10)alkyl, cycloaliphatic, and heterocyclic;
(2) compounds having the formula wherein R and R2 are individually selected from the group consisting of hydrogen, C1-C10 alkyl, aryl, and aryl-(C1-C10)alkyl with the proviso that R1 and R2 cannot both be hydrogen; and (3) combination thereof.
18. The method of claim 17 wherein said herbicide is oil soluble or oil miscible.
19. The method of claim 17 wherein said herbicide comprises a compound selected from the group consisting of herbicidally-active phenoxy acids; esters; and combinations thereof.
20. The method of claim 17 wherein said herbicide comprises a compound selected from the group consisting of 2,4-dichlorophenoxypropionic acid, butoxy-ethanol ester, 2,4-dichlorophenoxyacetic acid, butoxy-ethanol ester, 2,4,5-trichlorophenoxyacetic acid, butoxy ethanol ester, 2-(2,4,5-trichlorophenoxy)propionic acid, 4-(2,4-dichlorophenoxy)butyric acid, 4-chloro 2 methylphenoxyacetic acid, 4-(2-methyl 4-chlorophenoxy)butyric acid, and 2-(4-chloro-2-methylphenoxy)propionic acid, 4-amino-3,5,6-trichloropicolinic acid, 2-methoxy-3,6-dichlorobenzoic acid, 3,5,6-trichloro-2-pyridinyloxyacetic acid, and combinations thereof.
21. The method of claim 17 wherein said herbicide comprises a mixture of 2,4-dichloro-phenoxypropionic acid, butoxyethanol ester and 2,4-dichlorophenoxyacetic acid, butoxyethanol ester.
22. The method of claim 17 wherein said herbicide comprises 2,4,5-trichlorophenoxyacetic acid, butoxyethanol ester.
23. The method of claim 17 wherein said penetrant-carrier comprises a compound selected from the group consisting of triphenyl phosphate;
tricresyl phosphate; cresyl diphenyl phosphate;
2-ethylhexyl diphenyl phosphate; dibutyl phosphate;
tributyl phosphate; tridecyl phosphate; triethyl phosphate; tri(2-ethylhexyl) phosphate;
S,S,S,-tributylphosphorotrithioate; tributyl phosphorotrithioite; dibutyl phthalate; and dioctyl phthalate.
24. The method of claim 17 wherein said penetrant-carrier is tributyl phosphate.
25. The method of claim 17 wherein said mixture additionally contains an organic solvent diluent.
26. The method of claim 25 wherein said diluent comprises naphthenic oil.
27. The method of claim 17 wherein the ratio of said herbicide to said penetrant-carrier is from about 1:30 to about 20:1.
28. The method of claim 27 wherein said ratio is from about 1:10 to about 2:1.
29. The method of claim 27 wherein said ratio is from about 1:1.5 to about 1.5:1.
30. The method of claim 25 wherein the ratio of said diluent to said herbicide is from about 0 to about 25.
31. The method of claim 30 wherein said ratio is from about 0.2 to about 10.
32. The method of claim 30 wherein said ratio is from about 0.5 to about 4.
CA000440944A 1982-12-27 1983-11-10 Concentrated basal spray Expired CA1208929A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45316782A 1982-12-27 1982-12-27
US453,167 1982-12-27

Publications (1)

Publication Number Publication Date
CA1208929A true CA1208929A (en) 1986-08-05

Family

ID=23799445

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000440944A Expired CA1208929A (en) 1982-12-27 1983-11-10 Concentrated basal spray

Country Status (5)

Country Link
JP (1) JPS59152301A (en)
CA (1) CA1208929A (en)
GT (1) GT198304472A (en)
NZ (1) NZ206709A (en)
ZA (1) ZA839580B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT2833715T (en) * 2012-04-02 2019-06-05 Dow Agrosciences Llc Aromatic esters for controlling agricultural spray drift

Also Published As

Publication number Publication date
JPS6352001B2 (en) 1988-10-17
GT198304472A (en) 1985-06-19
NZ206709A (en) 1986-07-11
ZA839580B (en) 1984-08-29
JPS59152301A (en) 1984-08-31

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