Biochemical Degradation of Cyanamide and Dicyandiamide

Estermaier, Lydia M.; Sieber, Axel; Lottspeich, Friedrich; Matern, Dipl.-Chem. Dagmar H. M.; Hartmann, Guido

doi:10.1002/anie.199206201

Cited by 20 publications

(10 citation statements)

References 23 publications

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“…cyanamide, according to the situation depicted in 2. Interest in this study also arose from the fact that cyanamide itself has been recognized as a substrate for both urease (yielding carbon dioxide and ammonia) [8] and Mo-nitrogenase, [9] implying its as-yet-unresolved binding to these multimetallic enzyme active sites. Unexpectedly however, several different binding modes of nitrile moieties at the bimetallic core were found in the course of these investigations, among them an intriguing coordination of cyanoguanidine (the dimeric form of cyanamide) within the clamp of the two metal ions.…”

Section: Introductionmentioning

confidence: 98%

Cooperative Binding of Nitrile Moieties Within a Bimetallic Pocket: Enforcing Side-On π-Interaction With a High-Spin Nickel(II) Site

Meyer¹,

Hyla‐Kryspin²,

Kaifer³

et al. 2000

Eur. J. Inorg. Chem.

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Section: Introductionmentioning

confidence: 98%

Cooperative Binding of Nitrile Moieties Within a Bimetallic Pocket: Enforcing Side-On π-Interaction With a High-Spin Nickel(II) Site

Meyer¹,

Hyla‐Kryspin²,

Kaifer³

et al. 2000

Eur. J. Inorg. Chem.

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“…Studies have revealed that the inhibitory potential of dicyandiamide (DCD) can curb nitrate leaching by up to 76% (Di and Cameron, 2004) and N 2 O emissions by up to 70% (Di et al, 2007). Yet for all its effectiveness, degradation in soil limits the persistence of DCD (Estermaier et al, 1992), which has a half-life estimated between 110 d at 5°C and approximately 20 d at 25°C (Kelliher et al, 2008). Consequently, repeated soil applications are required to maintain efficacy.…”

Section: Introductionmentioning

confidence: 99%

Slow delivery of a nitrification inhibitor (dicyandiamide) to soil using a biodegradable hydrogel of chitosan

et al. 2013

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h i g h l i g h t sDicyandiamide (DCD) was encapsulated in glyoxal-crosslinked chitosan hydrogel beads. Chitosan delayed the release of nitrification inhibitor DCD in water and soil. DCD release was controlled by glyoxal polymerisation inside chitosan. The higher glyoxal polymerisation the more delayed DCD release in water or in soil. The higher glyoxal polymerisation the less DCD encapsulated in the beads. a r t i c l e i n f o b s t r a c tUsing chemical inhibitors to reduce soil nitrification decreases emissions of environmental damaging nitrate and nitrous oxide and improves nitrogen use efficiency in agricultural systems. The efficacy of nitrification inhibitors such as dicyandiamide (DCD) is limited in soil due to biodegradation. This study investigated if the persistence of DCD could be sustained in soil by slow release from a chitosan hydrogel. DCD was encapsulated in glyoxal-crosslinked chitosan beads where excess glyoxal was (i) partly removed (C beads) or (ii) allowed to dry (CG beads). The beads were tested in water and in soil. The beads contained two fractions of DCD: one which was quickly released in water, and one which was not. A large DCD fraction within C beads was readily available: 84% of total DCD bead content was released after 9 h immersion in water, while between 74% and 98% was released after 7 d in soil under low to high moisture conditions. A lower percentage of encapsulated DCD was readily released from CG beads: 19% after 9 h in water, and 33% after 7 d in soil under high rainfall conditions. Kinetic analysis indicated that the release in water occurred by quasi-Fickian diffusion. The results also suggest that DCD release was controlled by bead erosion and the leaching of glyoxal derivatives, predominantly a glyoxal-DCD adduct whose release was positively correlated with that of DCD (R 2 = 0.99, p 6 0.0001). Therefore, novel chitosan/glyoxal composite beads show a promising slow-release potential in soil for agrochemicals like DCD.

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“…2003). This finding is surprising because cyanamide has long been believed to be absent in nature (Estermaier et al . 1992; Maier‐Greiner et al .…”

Section: Introductionmentioning

confidence: 97%

Biosynthetic origin of the nitrogen atom in cyanamide inVicia villosasubsp.varia

Kamo

Kato

Abe

et al. 2009

Soil Science and Plant Nutrition

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Natural cyanamide (NH 2 CN) has recently been found in three Leguminosae plants: Vicia villosa subsp. varia, Vicia cracca and Robinia pseudo-acacia. As cyanamide has long been thought to be absent in nature, its physiological role and biosynthesis are totally unknown. N]-glutamine, indicating that these nitrogenous compounds are distant precursors of cyanamide. Although the guanidino group of l-arginine (-NH-C(NH 2 )=NH) and urea (NH 2 C(=O)NH 2 ) were candidate precursors of cyanamide on the basis of structural similarity, direct incorporation of the guanidino group of l-[ 13 C 6 , 15 N 4 ]-arginine and [ 13 C, 15 N 2 ]urea into cyanamide was not observed. These results eliminated the possibility that cyanamide is biosynthesized by the addition of ammonia to an electrophilic carbon or by the conversion of the tested compounds that were structurally relevant to cyanamide.

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Biochemical Degradation of Cyanamide and Dicyandiamide

Abstract: Leopoldshafen 2 (FRG) on quoting the depository number CSD-56193, the names of the authors, and the journal citation.

Cited by 20 publications

References 23 publications

Cooperative Binding of Nitrile Moieties Within a Bimetallic Pocket: Enforcing Side-On π-Interaction With a High-Spin Nickel(II) Site

Cooperative Binding of Nitrile Moieties Within a Bimetallic Pocket: Enforcing Side-On π-Interaction With a High-Spin Nickel(II) Site

Slow delivery of a nitrification inhibitor (dicyandiamide) to soil using a biodegradable hydrogel of chitosan

Biosynthetic origin of the nitrogen atom in cyanamide inVicia villosasubsp.varia

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