Wettable powder formulations of herbicides

Details Wettable powder formulations of herbicides Wettable powder formulations of herbicides

1996-11-19

2003-12-02

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C504S110000, C504S235000, C504S258000, C504S270000, C504S323000, C504S358000

Reexamination Certificate

active

06656883

ABSTRACT:

This application has been filed under 35 USC 371 as the National stoge of International application PCT/IB95/00001, filed Jan. 3, 1995.
The present invention relates to a wettable powder formulation of solid herbicides on a solid carrier material and large amounts of a nonionic surfactant which is a reaction product of an alcohol with longer chain length and identical or different alkylene oxides, and whose end groups may additionally be alkylated.
Pesticides are usually marketed as formulated concentrates. In addition to water-dispersible powders, it is also possible to use suspension concentrates, emulsifiable concentrates or other physical forms, as described, inter alia, in EP-B-0 190 995. Emulsifiable concentrates consist essentially of a concentrated solution of the active ingredient in a suitable organic solvent, typically a mineral oil or xylene, which can be emulsified in water by adding suitable surfactants. They usually have very good biological activity and are easily to handle when formulating the spray mixture. One disadvantage is the use of an organic solvent.
Water-dispersible and wettable powders typically consist of inert carrier materials, one or more active ingedients, and surface active compounds that ensure easily wettability with water. Organic solvents are not required. It is frequently observed that these powders have a markedly lower biological activity than emulsifiable concentrates, so that this type of formulation is impracticable, i.e. it must be used in too high concentration.
Nonionic surfactants derived from fatty alcohol ethoxylates may also be used for formulating wettable powders. Usually, however, only minor amounts of surfactant are used, as the powders are required to be readily flowable and must remain storage-stable over a considerable period of time. On contact with water, no lumps shall form and the powder must form a fine dispersion as rapidly as possible when stirred in water.
C. L. McGiness, P. J. Porpiglia and G. R. Gillespie report in Abstr. Meet. Weed Sci. Soc. Am. (32, 13, 1992) on greater biological control when using primisulfuron in admixture with ethoxylated fatty alcohols. The fatty alcohol ethoxylate preferably consists of a 70% ethoxylated C
12
-C
14
fatty alcohol. The fatty alcohol ethoxylate is mixed direct with the herbicide, the mixture is diluted with water and then applied in a greenhouse.
A wettable powder useful in practice having a high content of fatty alcohol ethoxylate and very good biological properties has so far not been disclosed.
It has now been found that storage-stable wettable powders of high biological activity can be obtained by applying herbicidally active compounds together with large amounts of an alkylene-oxylated alcohol with longer chain length as nonionic surfactant on a solid porous carrier material, even if said nonionic surfactant carries alkylated end groups. Accordingly, in one of its aspects the invention relates to a formulation comprising
a) at least one herbicide,
b) at least one porous solid carrier material, and
c) a nonionic surfactant,
which formulation contains 30 to 60% by weight, based on the total formulation, of at least one nonionic surfactant of formula I
R
1
—(O—R
2
—)
n
O—R
3
  (I)
wherein R
1
is C
8
-C
16
alkyl or C
8
-C
16
alkenyl, R
2
is identical or different C
2
-C
4
alkylene, R
3
is hydrogen or C
1
-C
4
alkyl, and n is an integer from 5-10.
Suitable herbicides are known per se and described, inter alia, in R. Wegler, Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel (Chemistry of Plant Protection Agents and Pesticides), Volume 2, Springer Verlag 1970, pp. 196-390.
Preferred herbicides are those selected from the groups consisting of the urea derivatives, imidazolinones, sulfonylureas, uracils, cyclohexanediones, chloroacetanilides, oxime ethers, triazines and phenoxypropionic acid derivatives.
Particularly preferred herbicides are those of the group of phenoxypropionic acid derivatives disclosed, inter alia, in EP 0 083 556. They are particularly useful active ingredients for the wettable powders of this invention.
Another preferred group of herbicides is that of the group of the sulfonylureas disclosed, inter alia, in EP-A-0 044 807 or in EP-A-0 120 814.
The novel formulations may additionally comprise safeners, typically those of the group of the quinoline derivatives. Particularly preferred safener-herbicide combinations are disclosed, inter alia, in EP-A-0 191 736 or in EP-A-0 094 349.
Particularly preferred herbicides are compounds of formula II which may be in the form of the R enantiomer or the racemate
wherein Q is a radical of formula
wherein R
4
is hydrogen, F, Cl or Br;
R
5
is CF
3
, CN, Cl, Br or I;
R
7
and R
8
are each independently of the other F, Cl, Br, I, CF
3
or CN,
X is oxygen or sulfur, and n is 0 or an integer from 1 to 3;
Z is a radical of formula
wherein R
6
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, C
3
-C
8
haloalkynyl, or C
1
-C
6
alkyl which is substituted by CN, NO
2
, C
1
-C
4
alkoxy, C
1
-C
4
alkyl-SO—, C
1
-C
4
alkyl-SO
2
—, C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, C
3
-C
8
alkynyloxycarbonyl, C
1
-C
4
alkylidene-aminooxy or N(R
10
)(R
11
), or is C
3
-C
8
alkenyl;
R
9
alkyl, haloalkyl, CN or C
1
-C
4
alkoxycarbonyl;
and R
10
and R
11
are each independently of the other C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, phenyl, benzyl or phenyl or benzyl, each substituted by halogen, NO
2
, CN, OCH
3
, or CF
3
, or R
10
and R
11
, together with the linking nitrogen atom, form a 5-7-membered saturated heterocycle.
Alkyl in R
6
, R
9
, R
10
and R
11
may be linear or branched and, in the significance of C
1
-C
8
alkyl, is typically ethyl, the different isomers of propyl, butyl, pentyl, hexyl, heptyl or octyl.
Alkenyl in R
6
, R
10
and R
11
may be linear or branched and in the significance of C
3
-C
8
alkenyl is typically the different isomers of propenyl, butenyl, pentenyl, hexenyl, heptenyl or octenyl. Alkenyl is preferably C
2
-C
7
alkenyl-CH
2
—.
Alkynyl may be linear or branched and in the significance of C
3
-C
8
alkynyl is typically the different isomers of propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkynyl is preferably C
2
-C
7
alkynyl-CH
2
—,
C
1
-C
4
Alkoxy is typically methoxy, ethoxy, propoxy or butoxy. C
1
-C
4
Alkylthio may be methylthio, ethylthio, propylthio or butylthio.
The 3-8-membered N-heterocycle is preferably morpholino or piperidino.
Very particularly preferred herbicides are compounds of formula III or IV
especially in the R-configuration.
Further preferred compounds are those of formula V, VI or VII.
Suitable safeners are a number of the quinoline derivatives disclosed in the references cited hereinabove. A compound of formula
is particularly suitable.
The aforementioned compounds of Formulae III-VIII have the following common names in the art:
III clodinafop-propargyl
IV propaquizafop
V fluazifop-butyl
VI fenoxaprop-ethyl
VII quizalofop-ethyl
VIII cloquintocet-mexyl.
The herbicides can be used in an amount of 1 to 30% by weight, preferably of 5 to 15%, based on the entire formulation.
If a safener is concurrently used, the ratio of safener to herbicide is 1:5 to 5:1, preferably 1:4 to 1:1.
Herbicide and safener usually have an average particle size of 1:100, preferably of 1:50 and, most. preferably, of 1 to 25 &mgr;m.
The solid carriers are porous and preferably have an inner surface area of at least 10 m
2
/g, preferably 20 to 400 m
2
/g and, most preferably, 20 to 200 m
2
/g. Solid carriers for wettable powders are usually natural mineral fillers such as calcite, talcum, kaolin, diatomaceous earth, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid, synthetic highly absorbent silicic acid, or porous polymers such as urea/formaldehyde condensate (Pergopak). Suitable granulated adsorptive carriers are porous types such as pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carrie

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