Stockholders' Equity (Tables)

12 Months Ended

Dec. 31, 2022

Share-Based Payment Arrangement [Abstract]

Stock Option Activities of Long-Term Incentive and Option Plans

The following information relates to our long-term incentive plans:

	December 31, 2022
	2016 Plan		2008 Plan
Maximum number of securities for issuance		5,750,000
Number of awards available to be granted (1)		2,425,376
Number of unvested restricted stock/performance-based    restricted stock/restricted stock units outstanding		1,443,502		—
Number of options outstanding		—		13,000
Number of options exercisable		—		13,000

.

(1)Includes 2008 and 2016 Plan shares canceled, forfeited, expired unexercised, which became available for reissuance under the 2016 Plan.

A summary of stock option activity in 2022 is presented below:

	2022
	Shares		Weighted-Average Exercise Price
Outstanding at beginning of year		13,000	$	25.66
Granted		—	$	—
Exercised		—	$	—
Forfeited or expired		—	$	—
Outstanding at end of year		13,000	$	25.66
Exercisable at end of year		13,000	$	25.66

	2022		2021		2020
Stock-based compensation expense - Cost of sales	$	—	$	—	$	106,000
Stock-based compensation expense - SG&A	$	—	$	—	$	42,000
Income tax benefit	$	—	$	—	$	(36,000	)
Total intrinsic value of options exercised during the year	$	—	$	—	$	—
Total fair value of options vested during the year	$	—	$	—	$	—
Total intrinsic value of options outstanding at end of year	$	—	$	—	$	—
Total intrinsic value of options exercisable at end of year	$	—	$	—	$	—
Total weighted-average remaining vesting period in years		—		—		—
Total weighted-average remaining contractual life period in years (options outstanding)		1.92		2.92		2.64
Total weighted-average remaining contractual life period in years (options exercisable)		1.92		2.92		2.64

Summary of Restricted Stock Activity

A summary of restricted stock activity during 2022 is presented below:

	Restricted Stock					Performance-Based Restricted Stock					Restricted Stock Units					Performance Based Restricted Stock Units
	Shares			Weighted- Average Grant Date Fair Value		Shares			Weighted- Average Grant Date Fair Value		Shares			Weighted- Average Grant Date Fair Value		Shares		Weighted- Average Grant Date Fair Value
Unvested outstanding beginning of year		948,979		$	2.78		742,264		$	2.67		209,743		$	5.04		—	$	—
Granted		—		$	—		—		$	—		264,800		$	13.15		161,922	$	13.22
Vested		(402,485	)	$	3.74		(429,625	)	$	2.65		—		$	—		—	$	—
Cancelled or forfeited		—		$	—		—		$	—		(52,096	)	$	6.73		—	$	—
Unvested outstanding end of year		546,494		$	2.72		312,639		$	2.71		422,447		$	10.50		161,922	$	10.40

	Restricted Stock
	2022 (1)			2021			2020
Shares of restricted stock granted		—			799,500			40,479
Total fair value of restricted stock granted	$	—		$	2,183,000		$	87,000
Weighted-average fair value per restricted stock granted during year	$	—		$	3.55		$	2.15
Stock-based compensation expense - Cost of sales	$	95,000		$	107,000		$	62,000
Stock-based compensation expense - SG&A	$	1,047,000		$	1,645,000		$	1,078,000
Income tax benefit	$	(269,000	)	$	(430,000	)	$	(279,000	)
Total weighted-average remaining vesting period in years		0.98		1.84				1.61
Total fair value of restricted stock vested during the year	$	4,394,000		$	2,729,000		$	578,000

	Performance-Based Restricted Stock
	2022 (1)			2021 (2)			2020 (2)
Shares of PBRS granted		—			675,532			398,134
Total fair value of PBRS granted	$	—		$	2,480,000		$	980,000
Weighted-average fair value per PBRS granted during year	$	—		$	3.09		$	2.46
Stock-based compensation expense - Cost of sales	$	70,000		$	103,000		$	-
Stock-based compensation expense - SG&A	$	670,000		$	2,938,000		$	218,000
Income tax benefit	$	(174,000	)	$	(747,000	)	$	(53,000	)
Total weighted-average remaining vesting period in years		0.91			1.56			1.57
Total fair value of PBRS vested during the year	$	4,976,000		$	6,671,000		$	—

	Restricted Stock Units
	2022			2021			2020
Shares of RSU granted		264,800			327,188			301,361
Total fair value of RSU granted	$	3,482,000		$	1,653,000		$	255,000
Weighted-average fair value per RSU granted during year	$	13.15		$	5.05		$	0.85
Stock-based compensation expense - Cost of sales	$	297,000		$	161,000		$	-
Stock-based compensation expense - SG&A	$	1,229,000		$	562,000		$	255,000
Income tax benefit	$	(359,000	)	$	(178,000	)	$	(63,000	)
Total weighted-average remaining vesting period in years		1.71			2.42			0.48
Total fair value of RSU vested during the year	$	—		$	2,209,000		$	16,000

(1)We did not grant any restricted stock or performance based restricted stock awards during 2022.

(2)Upon the change of control event associated with the exchange of the Series E and Series F Redeemable Preferred discussed in Note 1, during 2021 such PBRS are subject only to the time-based vesting conditions set forth in the applicable award agreement and the 2016 Plan.

	Performance-Based Restricted Stock Units
	2022
Shares of PBRSU granted		161,922
Total fair value of PBRSU granted	$	2,141,000
Weighted-average fair value per PBRSU granted during year	$	13.22
Stock-based compensation expense - Cost of sales	$	50,000
Stock-based compensation expense - SG&A	$	567,000
Income tax benefit	$	(145,000	)
Total weighted-average remaining vesting period in years		1.99
Total fair value of PBRSU vested during the year	$	—

The PBRSU grants are tied to the total stockholder return of the fair market value of our common stock (“TSR”) and fixed costs per ton of ammonia (“FC”) measured annually over a three-year period. The TSR and FC goals utilize annual target share amounts based on 1/3 of the total target award for each grant. The annual goals include payout factors for both the TSR and FC goals. The payout factors are based on the actual results. The payout factors include a minimum threshold (if not met, no shares will be banked for that specific goal) and a maximum ceiling for each of the three year periods within the grant. As a result, the number of shares earned annually could be lower or higher than the annual target PRBSU shares. The annual goals are independently earned and are not affected by the performance goals attained in the other periods. Banked shares are used in the final calculation to determine the vested shares. These awards granted require the grantee to be continuously employed through the end of the term for vesting purposes.

The estimated fair value of the FC is based on the closing price of our common stock on the day preceding the grant date. We estimate the fair value of each PBRSU TSR on the date of grant using a Monte Carlo simulation with the following assumptions:

•the closing stock price on the day preceding the grant,

•the prediction time horizon, the vesting term of the grant,

•the three-year Treasury yield curve rate on the grant date,

•the standard deviation of historical daily returns for the length of the vesting term of the grant.