Use of low-volatility pyrazole derivatives having hydrophilic groups as nitrification inhibitors

• US 5,972,064 A
• Filed: 08/06/1997
• Issued: 10/26/1999
• Est. Priority Date: 02/06/1995
• Status: Expired due to Term

• Current Assignee: Eurochem Agro GmbH
• Original Assignee: BASF AG (BASF SE)
• Inventors: Gold, Randall Evan, Rittinger, Stefan, Dressel, Jurgen, Rieber, Norbert
• Primary Examiner(s): Richter, Johann
• Assistant Examiner(s): KEATING, DOMINIC J
• Application Number:
  US08/875,755
• Time in Patent Office: 811 Days
• Field of Search: 548/377.1, 548/376.1, 548/372.1, 548/377.5, 71/27
• US Class Current: 71/27
• CPC Class Codes: C05G 3/90 for affecting the nitrification of ammonium compounds or urea in the soil
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/16 Halogen atoms or nitro radicals
• CPC Class Codes: Y02P 60/21 Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures

Abstract

The present invention provides pyrazole compounds which are useful as nitrification inhibitors.

Claims

1. A method for nitrification inhibition, which comprises applying to a soil a pyrazole compound of the general formula I ##STR17## or an acid addition salt thereof, wherein the groups R¹, R², R³ and R⁴ have the following meanings:

R¹, R² and R³ are halogen, nitro, hydrogen, C₁ - to C₂₀,-alkyl, C₃ - to C₈ -cycloalkyl, C₅ -to C₂₀ -aryl or alkylaryl, wherein the C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl is, optionally, monosubstituted or disubstituted by halogen and/or hydroxy,

R⁴ is a (group R^4a having the formula II ##STR18## wherein R⁵ and R⁶ are hydrogen, C₁ - to C₂₀ -alkyl which is, optionally, monosubstituted or disubstituted by halogen and/or hydroxyl, a carboxyl group which may be neutralized to form a salt, a carboxymethyl group, a C₁ - to C₆ -alkoxycarbonyl group which may be mono- or di-substituted by C₁ -C₆, alkyl groups, or a C₁ to C₆ -carbamoyl group which may be mono- or di-substituted by C₁ -c₆ -alkyl groups,

or R⁵ and R⁶ together form a carbonyldioxy (group and

R⁷ is a carboxyl group.

2. The method of claim 1, wherein the groups R¹, R², R³ are C₁ - to C₅ -alkyl or halogen.

3. A pyrazole compound of the formula la ##STR19## wherein R¹ and R³ are nitro, hydrogen, C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl, wherein the C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl is, optionally, monosubstituted or disubstituted by halogen and/or hydroxy,

R² is halogen, and

R^4a is a group having the formula II ##STR20## where R⁵ and R⁶ are hydrogen, C₁ - to C₂₀ -alkyl which is, optionally, monosubstituted or disubstituted by halo(en and/or hydroxyl, a carboxyl group which may be neutralized to form a salt, a carboxymethyl group, a C₁ - to C₆ -alkoxycarbonyl group which may be mono- or di-substituted by C₁ -C₆ -alkyl groups, or a C₁ to C₆ -carbamoyl group which may be mono- or di-substituted by C₁ -C₆ -alkyl groups

or R⁵ and R⁶ together form a carbonyldioxy group and

R⁷ is a carboxyl group,

or an acid addition salt thereof.

4. The compound of claim 3, wherein

R⁵ is hydrogen;

and

R⁶ is hydrogen or a carboxyl group or a substituent capable of being converted into a carboxyl group.

5. A process for preparing pyrazole compounds of claim 3, which comprises reacting a pyrazole compound of the formula Va ##STR21## where R^x and R^z are halogen, nitro, hydrogen, C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl, wherein C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl is, optionally, monosubstituted or disubstituted by halogen and/or hydroxyl, and

R^ya is halogen

with a compound of the formula VI ##STR22## where R¹³ is chlorine or bromine, those compounds being excluded where 2 of the groups R^x, R^z or R^ya are simultaneously halogen, wherein R⁵, R⁶, and R⁷ are defined in claim 3.

6. A process for preparing compounds of claim 4, comprising reacting a pyrazole compound of the formula Va ##STR23## wherein R^x and R^z are halogen, nitro, hydrogen, C₁ - to C₂₀ -alkyl, C₃ to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl, wherein the C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl is, optionally, monosubstituted or disubstituted by halogen and/or hydroxyl, and

R^ya is halogen,

wherein compounds in which 2 of the groups R^x, R^z or R^ya are simultaneously halogen are excluded,

with a compound of the formula VII ##STR24## where R⁶ is hydrogen, a carboxyl group or a substituent capable of being converted into a carboxyl group;

R¹⁴ is a carboxyl group or a substituent capable of being converted into a carboxyl group and

R¹⁵ is hydrogen or methyl.

8. A fertilizer comprising:

(a) a mineral fertilizer, and

(b) 100 to 10000 ppm by weight, based on the weight of the mineral fertilizer, of pyrazole compound of claim 3.

9. A method of inhibiting nitrification, comprising applying to a soil an effective amount of the pyrazole compound of claim 3 to inhibit nitrification.

7. A fertilizer composition comprising:

(a) a mineral fertilizer, and

(b) 100 to 10000 ppm by weight, based on the weight of the mineral fertilizer, of a pyrazole compound of formula I ##STR25## or an acid addition salt thereof, where the groups R¹, R², R³ and R⁴ have the following meanings;

R¹, R² and R³ are halogen, nitro, hydrogen, C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ -to C₂₀ -aryl or alkylaryl, wherein the C₁ - to C₂₀ -alkyl, C₃ - to C₈ -cycloalkyl, C₅ - to C₂₀ -aryl or alkylaryl is, optionally, monosubstituted or disubstituted by halogen and/or hydroxy,

R⁴ is a group R^4a having the formula II ##STR26## wherein R⁵ and R⁶ are hydrogen, C₁ - to C₂₀ -alkyl which is, optionally, monosubstituted or disubstituted by halogen and/or hydroxyl, a carboxyl group which may be neutralized to form a salt, a carboxymethyl group, a C₁ - to C₆ -alkoxycarbonyl (group which may be mono- or di-substituted by C₁ -C₆ alkyl groups, or a C₁ to C₆ -carbamoyl group may be mono- or di-substituted by C₁ -C₆ -alkyl groups,

or R⁵ and R6 together form a carbonyldioxy group and

R⁷ is a carboxyl group.