Organic Ammonium Salts Of Anionic Pesticides

Abstract

The invention relates to an organic ammonium salt of formula (I), wherein the symbols have the following meanings: A- is an anionic pesticide, R.sup.1 is H, C.sub.1C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH; R is H, CH.sub.3 or two adjacent radicals R together form a group —C(R′)— and R′ is equal to or different from H or CH.sub.3, wherein said salt is suitable for reducing the volatility of active substances in the spray application of anionic pesticides.

##STR00001##

Claims

1. An organic ammonium salt of the formula (I) ##STR00005## where the symbols have the following definitions: A.sup.− is an anionic pesticide, R.sup.1 is H, C.sub.1-C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH; R is H, CH.sub.3, or two adjacent R radicals together form a —C(R′)— group and R′ is the same or different and is H or CH.sub.3.

2. An ammonium salt as claimed in claim 1, where A.sup.− is the conjugate base of a pesticidal Bronsted acid having a pK.sub.a in the range from 1.5 to 7, preferably 2 to 6 and more preferably 2.5 to 5.

3. An ammonium salt as claimed in claim 1 or 2, wherein A is selected from the group consisting of: acifluorfen, aminocyclopyrachlor, aminopyralid, amitrol, asulam, benazolin, bentazon, bialafos, bensulfuron, bispyribac, bromacil, bromoxynil, bicyclopyron, chlorflurenol, chlorthal, clodinafop, cloprop, clopyralid, 4-CPA, 4-CPB, 4-CPP, cyhalofop, 2,4-D, dalapon, 2,4-DB, 3,4-DA, 3,4-DB, 3,4-DP, 2,4,5-T, 2,4,5-TB, dicamba, dichlorprop, dichlorprop-P, diflufenzopyr, diclofop, endothal, fenoprop, fenoxaprop, fenthiaprop, flamprop, flamprop-M, florasulam, fluazifop, fluazifop-P, flucarbazone, flufenpyr, flumiclorac, fluoroglycofen, flupropanate, flurenol, fluroxypyr, fluthiacet, fomesafen, foramsulfuron, fosamine, glufosinate, glufosinate-P, glyphosate, halosulfuron, haloxyfop, haloxyfop-P, imizameth, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, isoxapyrifop, lactofen, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mesosulfuron, mesotrione, nicosulfuron, octanoic acid, oleic acid, pelargonic acid, picloram, primisulfuron, propaquizafop, propoxycarbazone, pyraflufen, pyriminobac, pyrithiobac, pyroxsulam, quinclorac, quinmerac, quizalofop, quizalofop-P, sulcotrione, sulfometuron, 2,3,6-TBA, TCA, tembotrione, thiencarbazone, topramezone, tricamba, triclopyr, trifopsic acid, abscisic acid, glyphosine, indole-3-acetic acid, indole-4-butyric acid, jasmonic acid, 1-naphthylacetic acid, 2-naphthylacetic acid, naphthyloxyacetic acid, prohexadione, salicylic acid, 2,3,5-triiodobenzoic acid, trinexapac, thuringiensin, insecticidal free keto-enols such as deacetylated/hydrolyzed spirotetramat or pinoxaden, fosetyl, polyoxorim and polyoxin D.

4. An ammonium salt as claimed in claim 3, wherein A is selected from the group consisting of bicyclopyron, bromoxynil, clopyralid, 2,4-D (2,4-dichlorophenoxyacetic acid), dicamba, diquat, florasulam, fomesafen, glufosinate, glyphosate, MCPA, mesotrione, nicosulfuron, pelargonic acid, quinclorac, quinmerac, salicylic acid, sulcotrione, tembotrione and triclopyr.

5. An ammonium salt as claimed in any of claims 1 to 4, where the symbols in the formula (I) have the following definitions: R.sup.1 is H, C.sub.1-C.sub.4-alkyl or CH.sub.2CH.sub.2OH and R is H or CH.sub.3.

6. An ammonium salt as claimed in any of claims 1 to 5, where the symbols in the formula (I) have the following definitions: R.sup.1 is H, CH.sub.3 or CH.sub.2CH.sub.2OH and R is H.

7. An ammonium salt as claimed in any of claims 1 to 6, where R.sup.1=CH.sub.3 and R=H or R.sup.1=CH.sub.2CH.sub.2OH and R=H.

8. A process for preparing an ammonium salt as claimed in any of claims 1 to 7, wherein the protonated form of an anionic herbicide is reacted with a glucamine of the formula (II) ##STR00006## where the symbols have the definitions given in the formula (I).

9. The use of an ammonium salt as claimed in any of claims 1 to 7 as a pesticide.

10. A pesticide composition comprising a) one or more ammonium salts (I) as claimed in any of claims 1 to 7 and b) one or more formulation auxiliaries.

11. The pesticide composition as claimed in claim 10 in the form of a herbicide composition.

12. The pesticide composition as claimed in claim 10 or 11, comprising, as formulation auxiliary b), one or more copolymers A) comprise, where the copolymers contain one or more structural units derived from a) 19.9% to 75.9% by weight of glycerol b) 0.1% to 30% by weight of at least one dicarboxylic acid and c) 24% to 80% by weight of at least one monocarboxylic acid of formula (III)
R.sup.2—COOH  (III) where R.sup.2 is (C.sub.5-C.sub.29) -alkyl; (C.sub.7-C.sub.29)-alkenyl; phenyl or naphthyl.

13. A method of controlling harmful organisms, wherein the harmful organism or its habitat is brought into contact with an ammonium salt (I) as claimed in any of claims 1 to 6 or a pesticide composition as claimed in claim 10 or 11.

14. The method as claimed in claim 13, wherein the harmful organisms are unwanted plants and the pesticide is a herbicide.

15. The use of an ammonium salt as claimed in any of claims 1 to 7 for reducing the liquid in the anionic pesticide present in salt form.

Description

WORKING EXAMPLES

Preparation

Preparation Example 1

[0146] 37 g of dicamba were suspended in 30 g of deionized water while stirring. Subsequently, 33 g of N-methyl-glucamine were introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 2

[0147] 37 g of dicamba were suspended in 30 g of deionized water while stirring. Subsequently, 33 g of dimethyl-glucamine were introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 3

[0148] 21 g of MCPA were suspended in 58 g of deionized water while stirring. Subsequently, 21 g of N-methyl-glucamine were introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 4

[0149] 20 g of pelargonic acid were suspended in 55 g of deionized water while stirring. Subsequently, 25 g of N-methylglucamine were introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 5

[0150] 20 g of pelargonic acid were suspended in 10 g of deionized water while stirring. Subsequently, 25 g of dimethylglucamine were introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 6

[0151] 0.21 g of mesotrione was suspended in 10 g of deionized water while stirring. Subsequently, 0.11 g of N-methylglucamine was introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 7

[0152] 0.13 g of nicosulfuron was suspended in 10 g of deionized water while stirring. Subsequently, 0.07 g of N-methylglucamine was introduced into the active ingredient suspension while stirring. The result was a clear solution.

Preparation Example 8

[0153] 0.11 g of nicosulfuron was suspended in 10 g of deionized water while stirring. Subsequently, 0.065 g of dimethylglucamine was introduced into the active ingredient suspension while stirring. The result was a clear solution.

Formulations

[0154] The composition of the active ingredient formulations from the preparation examples are summarized in table 1:

TABLE-US-00001 TABLE 1 Example (w %) Composition 1 2 3 4 5 6 7 8 Dicamba 37 37 0 0 0 0 0 0 MCPA 0 0 21 0 0 0 0 0 Pelargonic acid 0 0 0 20 20 0 0 20 Mesotrione 0 0 0 0 0 2 0 0 Nicosulfuron 0 0 0 0 0 0 1.3 1.1 NMG 33 0 21 25 0 1 0.7 0.65 DMG 0 33 0 0 25 0 0 25 Water 30 30 58 55 55 97 98 98.25 Appearance Clear Clear Clear Clear Clear Clear Clear Clear solution solution solution solution solution solution solution solution NMG = N-methylglucamine DMG = dimethylglucamine