Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Reexamination Certificate
1999-07-19
2001-10-23
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
C424S406000, C424S409000, C424S421000, C514S365000, C504S266000
Reexamination Certificate
active
06306417
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a wettable or water-soluble granular agrochemical composition with excellent disintegrability in water and high dispersion stability.
BACKGROUND ART
Wettable granular agrochemical formulations are agrochemical granules which can be completely or easily dispersed or dissolved in water and, as such, are superior to earlier wettable powders in terms of ease of handling, ease of weighing, dust prevention, and convenience in application. However, manufacture of such granular preparations according to the conventional production recipes for wettable powders causes various troubles such as poor disintegrability in water, thus failing to give a stable dispersion.
As excellent pesticidal agents, JP-A 157308/1991 discloses a large number of guanidine derivatives, typically the compound of the following formula (II), and their compositions.
Moreover, certain guanidine derivatives and agrochemical formulations containing them (dusts, wettable powders, granules, etc.) are described in JP-A 28860/1990, JP-A 109374/1991 and JP-A 200768/1991.
The above-mentioned compound (II) is poorly soluble in water with a solubility of not more than 0.0003 g/ml in water at 20° C. and the conventional wettable powders have a drawback that they do not disintegrate well in water, thus failing to give a stable dispersion.
Therefore, in order that the compound (II) shows a pesticidal action more efficiently, development of a wettable or soluble granular agrochemical composition with excellent disintegrability and dispersibility in water has been awaited in earnest.
DISCLOSURE OF INVENTION
The inventors of the present invention have made much research and discovered surprisingly that, in a wettable or soluble granular agrochemical formulation containing a guanidine derivative such as said compound (II), incorporation of an alkenylsulfonate and a carrier such as lactose, ammonium sulfate, sodium hydrogen carbonate or diatomaceous earth as a carrier results in remarkable improvements in disintegrability and dispersibility in water. The inventors have made further research on the basis of the above findings and have completed the present invention.
Namely, the present invention relates to:
(1) a wettable or water-soluble granular agrochemical composition which comprises a guanidine derivative of the formula:
wherein
R
1
represents a homocyclic or heterocyclic group which may optionally be substituted; n is 0 or 1;
R
2
represents hydrogen or a hydrocarbon group which may optionally be substituted; R
3
represents a primary, secondary, or tertiary amino group; X represents an electron attractive group; or a salt thereof, an alkenylsulfonate and a carrier,
(2) the agrochemical composition as described in (1) above, wherein the guanidine derivative of the formula (I) is the compound of the formula:
(3) the agrochemical composition as described in (1) above, wherein the carrier is one or more carriers selected from the group consisting of lactose, ammonium sulfate, sodium hydrogen carbonate, and diatomaceous earth,
(4) a wettable granular agrochemical composition which comprises 30 to 85 weight % of the guanidine derivative of the formula (I) as described in (1) above, or a salt thereof, 0.1 to 15 weight % of an alkenylsulfonate and 10 to 70 weight % of a carrier to the total composition,
(5) a water-soluble granular agrochemical composition which comprises 5 to 60 weight % of the guanidine derivative of the formula (I) as described in (1) above, or a salt thereof, 0.1 to 15 weight % of an alkenylsulfonate and 25 to 95 weight % of a carrier to the total composition,
(6) a method for producing the agrochemical composition as described in (1) above, which comprises mixing the guanidine derivative of the formula (I) as described in (1) above, or a salt thereof and an alkenylsulfonate with a carrier, and granulating them, and
(7) a method for controlling a pest which comprises diluting the agrochemical composition as described in (1) above with water and scattering the thus diluted composition in a field.
BEST MODE FOR CARRYING OUT THE INVENTION
The guanidine derivative (I) for use in the wettable or water-soluble granular agrochemical composition (hereinafter sometimes referred to briefly as “agrochemical composition”) of the present invention occurs as geometrical isomers, namely cis[Z (zusammen or together)]- and trans[E (entgegen or opposite)]-isomers, in respect of the geometrical orientation of X, and when R
2
is hydrogen and R
1
is a primary or secondary amino group, then tautomers are formed theoretically. All of such isomers are also included in the category of guanidine compound (I) or its salt.
The homocyclic or heterocyclic group of R
1
is a cyclic group containing the same atoms only or a cyclic group containing two or more different atoms, i.e., a cyclic hydrocarbon group or a heterocyclic group, respectively.
The cyclic hydrocarbon group of R
1
includes a C
3-14
cyclic hydrocarbon group, specifically include a non-aromatic cyclic hydrocarbon group such as a C
3-8
cycloalkyl group, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; and a C
3-8
cycloalkenyl group, e.g. cyclopropenyl, 1-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 1,4-cyclohexadienyl; and an aromatic cyclic hydrocarbon group such as a C
6-4
aryl group, e.g. phenyl, naphthyl such as 1- or 2-naphthyl, anthryl such as 1-, 2- or 9-anthryl, phenanthryl such as 1-, 2-, 3-, 4- or 9-phenanthryl or azulenyl such as 1-, 2-, 4-, 5- or 6-azulenyl. The preferred cyclic hydrocarbon groups are aromatic ones, e.g. C
6-14
aryl groups such as phenyl, etc.
The heterocyclic group of R
1
includes a 5- to 8-membered ring group containing one to five hetero atoms selected from oxygen atom, sulfur atom and nitrogen atom and its condensed ring group with a 5- to 8-membered carbon ring or a 5- to 8-membered heterocyclic ring. Examples of the heterocyclic group are thienyl (e.g. 2- or 3-thienyl), furyl (e.g. 2- or 3-furyl), pyrrolyl (e.g. 2- or 3-pyrrolyl), pyridyl (e.g. 2-, 3- or 4-pyridyl), oxazolyl (e.g. 2-, 4- or 5-oxazolyl), thiazolyl (e.g. 2-, 4- or 5-thiazolyl), pyrazolyl (e.g. 3-, 4- or 5-pyrazolyl), imidazolyl (e.g. 2-, 4- or 5-imidazolyl), isoxazolyl (e.g. 3-, 4- or 5-isoxazolyl), isothiazolyl (e.g. 3-, 4- or 5-isothiazolyl), oxadiazolyl (e.g. 3- or 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl), thiadiazolyl (e.g. 3- or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl), triazolyl (e.g. 1,2,3-triazolyl, 1,2,4-triazolyl), tetrazolyl (e.g. 1H- or 2H-tetrazolyl), pyridyl in which the nitrogen atom is oxidized (e.g. N-oxido-2-, 3- or 4-pyridyl), pyrimidinyl (e.g. 2-, 4- or 5-pyrimidinyl), pyrimidinyl in which one or both of the nitrogen atoms are oxidized (e.g. N-oxido-2-, 4- or 5-pyrimidinyl), pyridazinyl (e.g. 3- or 4-pyridazinyl), pyrazinyl, pyridazinyl in which one or both of the nitrogen atoms are oxidized (e.g. N-oxido-3- or 4-pyridazinyl), benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo[1,5-b]pyridazinyl, triazolo[
4
,
5
-b]pyridazinyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, oxadinyl (e.g. 1,4-oxadinyl), morpholinyl, thiazinyl (e.g. 1,4-thiazinyl, 1,3-thiazinyl), piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolidinyl, quinolidinyl, naphthyridinyl (e.g. 1,8-naphthyridinyl), purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiadinyl or phenoxazinyl. Preferred heterocyclic groups are 5- or 6-membered nitrogen-containing heterocyclic groups such as pyridyl (e.g. 2-, 3- or 4-pyridyl) or thiazolyl (e.g. 2-, 4- or 5-thiazolyl). The homocyclic or heterocyclic group of R
1
may possess one to five (preferably one) substituents which are the same or different. Examples of the substituents are a C
1-15
alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undec
Levy Neil S.
Takeda Chemical Industries Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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